Supporting Information for: General method of Suzuki Myiaura … · Supporting Information for: General method of Suzuki-Myiaura cross-coupling of 4-and 5-halo- 1,2,3-triazoles in

Supporting Information for:

General method of Suzuki-Myiaura cross-coupling of 4- and 5-halo-

1,2,3-triazoles in water

Pavel S. Gribanov,a,b Gleb A. Chesnokov,b Maxim A. Topchiy,a,b Andrey F. Asachenkoa,b

and Mikhail S. Nechaev*a,b

a A. V.Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences,

119991 Moscow, Leninskiy prospect 29, Russian Federation.

b M. V. Lomonosov Moscow State University, 119991 Moscow, Leninskie Gory 1 (3),

Russian Federation.

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2017

Contents

General information ...................................................................................................................... 4

Synthetic procedures ..................................................................................................................... 5

General procedure for the preparation of 1,4,5-trisubstituted-1,2,3-triazoles by Suzuki

reaction from 4- and 5-halo-1,2,3-triazoles in water.............................................................. 5

5-methyl-1-phenyl-4-p-tolyl-1H-1,2,3-triazole (3a) 6 ............................................................ 5

5-methyl-1,4-diphenyl-1H-1,2,3-triazole (3b) 6 ..................................................................... 5

5-methyl-1-phenyl-4-o-tolyl-1H-1,2,3-triazole (3c) .............................................................. 6

5-methyl-4-(naphthalen-1-yl)-1-phenyl-1H-1,2,3-triazole (3d) ............................................. 6

5-methyl-1-phenyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3e) ................................................ 7

4-(4-fluorophenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole (3f) 6a ........................................... 7

4-mesityl-5-methyl-1-phenyl-1H-1,2,3-triazole (3g) ............................................................. 8

1-(4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone (3h) .................................. 8

1,4-diphenyl-5-propyl-1H-1,2,3-triazole (3i) ......................................................................... 9

1-phenyl-5-propyl-4-p-tolyl-1H-1,2,3-triazole (3j) ............................................................... 9

4-(naphthalen-1-yl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3k) ........................................... 10

4-(3-nitrophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3l) ................................................ 10

4-(4-fluorophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3m) ........................................... 11

1-phenyl-5-propyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3n) ............................................... 11

1,5-diphenyl-4-p-tolyl-1H-1,2,3-triazole (3o)...................................................................... 12

4-(naphthalen-1-yl)-1,5-diphenyl-1H-1,2,3-triazole (3p) .................................................... 12

1-benzyl-5-methyl-4-phenyl-1H-1,2,3-triazole (3q) 6a, 7 ...................................................... 13

1-benzyl-5-methyl-4-p-tolyl-1H-1,2,3-triazole (3r) ............................................................. 13

1-benzyl-5-methyl-4-o-tolyl-1H-1,2,3-triazole (3s)............................................................. 14

1-benzyl-5-methyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole (3t) ............................................ 14

1-benzyl-4-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole (3u) ............................................ 15

1-benzyl-5-methyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3v) .............................................. 15

1-benzyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5a) 8 .......................................................... 16

1-benzyl-4,5-diphenyl-1H-1,2,3-triazole (5b) 8 ................................................................... 16

1-benzyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole (5c) 9 ......................................... 17

1,4-diphenyl-5-p-tolyl-1H-1,2,3-triazole (5d)...................................................................... 17

1-phenethyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5e) ....................................................... 18

1-phenethyl-4,5-diphenyl-1H-1,2,3-triazole (5f) 10 ............................................................. 18

1-methyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5g) ............................................................ 19

1-methyl-4,5-diphenyl-1H-1,2,3-triazole (5h) 11 ................................................................. 19

1-methyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole (5i) ........................................... 20

1-methyl-5-(3-nitrophenyl)-4-phenyl-1H-1,2,3-triazole (5j) ............................................... 20

5-(4-fluorophenyl)-1-methyl-4-phenyl-1H-1,2,3-triazole (5k) ............................................ 21

5-p-tolyl-4-(p-tolyloxymethyl)-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole (5l) ........ 21

NMR spectra ................................................................................................................................ 23

References..................................................................................................................................... 91

General information

All catalytic reactions were performed under ambient atmosphere. All arylboronic acids,

KOH, Bu4NBr were purchased from commercial sources and were used as received.

1,4-disubstituted-5-halo-1,2,3-triazoles 4a-i were synthesized according to literature

procedures by [3+2]-cycloaddition aryl azides with copper(I) acetylides followed by addition of

N-chlorosuccinimide, N-bromosuccinimide or I2 respectively.1

4-bromo-5-methyl-1-phenyl-1H-1,2,3-triazole 1a and 1-benzyl-4-bromo-5-methyl-1H-

1,2,3-triazole 1d were prepared according to published procedures. 2

4-chloro-1-phenyl-5-propyl-1H-1,2,3-triazole 1b and 4-chloro-1,5-diphenyl-1H-1,2,3-

triazole 1c and were prepared by reactions of corresponding bromomagnesium acetylide with

phenyl azide followed by addition of C2Cl6 as chlorinating agent. 3

1-benzyl-4-iodo-5-methyl-1H-1,2,3-triazole 1e was prepared by aromatic Finkelstein

reaction from 1-benzyl-4-bromo-5-methyl-1H-1,2,3-triazole 1d, 3 eq. of sodium iodide, 5 mol%

of copper(I) iodide and 10 mol% of DMEDA. 4

(THP-Dipp)Pd(cinn)Cl was prepared according to published procedure. 5

NMR spectra were obtained on a Bruker “Avance 600” (600 MHz 1H, 151 MHz 13C).

The chemical shifts are frequency referenced relative to the residual undeuterated solvent peaks.

Coupling constants J are given in Hertz as positive values regardless of their real individual

signs. The multiplicity of the signals is indicated as ‘‘s”, ‘‘d”, “t” or ‘‘m” for singlet, doublet,

triplet or multiplet, respectively. The abbreviation ‘‘br” is given for broadened signals.

Synthetic procedures

General procedure for the preparation of 1,4,5-trisubstituted-1,2,3-triazoles by Suzuki

reaction from 4- and 5-halo-1,2,3-triazoles in water.

A 5 ml round-bottomed flask, equipped with a magnetic stir bar and reflux condenser,

was charged with 0.5 mmol of corresponding 4- or 5-halo-1,2,3-triazole, 0.6 mmol of

arylboronic acid, 16 mg (0.05 mmol, 10 mol%) of TBAB, appropriate base (56 mg (0.85 mmol,

1.7 eq) of KOH or 129 mg (1.53 mmol, 3.06 eq) of NaHCO3) followed by addition of 0.8 ml of

boiling deionized water. The reaction flask was transferred to preheated oil bath (140 °C) and

stirred until melting of reaction mixture was observed. Then 3.3 mg (0.005 mmol, 1 mol%) of

(THP-Dipp)Pd(cinn)Cl was added to the reaction mixture and the reaction mixture was refluxed

for 8 h, cooled to room temperature and extracted with 3x10 ml of ethyl acetate. The organic

extract was evaporated to dryness to give a crude product. Purification by chromatography

(eluent – hexane : ethyl acetate 4:1 or 2:1) gave analytically pure product

5-methyl-1-phenyl-4-p-tolyl-1H-1,2,3-triazole (3a) 6

Following general procedure 3a was obtained from 4-bromo-5-methyl-1-phenyl-1H-

1,2,3-triazole and p-tolylboronic acid. Resulting solid was purified by chromatography to give

121 mg (97%) of 5-methyl-1-phenyl-4-p-tolyl-1H-1,2,3-triazole as light-yellow solid.

Rf (CH2Cl2): 0.15.

1H NMR (600 MHz, Chloroform-d) δ 7.68 (d, J = 8.1 Hz, 2H), 7.59 – 7.54 (m, 2H), 7.54

– 7.49 (m, 3H), 7.29 (d, J = 7.9 Hz, 2H), 2.47 (s, 3H), 2.41 (s, 3H).

13C{1H} NMR (151 MHz, Chloroform-d) δ 145.0, 137.7, 136.6, 129.6, 129.6 , 129.5,

128.6, 127.2, 125.4, 21.4, 10.4.

5-methyl-1,4-diphenyl-1H-1,2,3-triazole (3b) 6

Following general procedure 3b was obtained from 4-bromo-5-methyl-1-phenyl-1H-

1,2,3-triazole and phenylboronic acid. Resulting solid was purified by chromatography to give

97 mg (83%) of 5-methyl-1,4-diphenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.13.


– 7.45 (m, 5H), 7.38 (t, J = 7.4 Hz, 1H), 2.49 (s, 3H).

13C{1H} NMR (151 MHz, Chloroform-d) δ 145.0, 136.5, 131.5, 129.8, 129.7, 129.6,

128.9, 127.9, 127.4, 125.4, 10.4.

5-methyl-1-phenyl-4-o-tolyl-1H-1,2,3-triazole (3c)

Following general procedure 3c was obtained from 4-bromo-5-methyl-1-phenyl-1H-

1,2,3-triazole and o-tolylboronic acid. Resulting solid was purified by to give 124 mg (99%) of

5-methyl-1-phenyl-4-o-tolyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.18.

1H NMR (600 MHz, Chloroform-d) δ 7.58 – 7.48 (m, 5H), 7.35 – 7.24 (m, 4H), 2.38 (s,

3H), 2.28 (s, 3H).

13C{1H} NMR (151 MHz, Chloroform-d) δ 145.6 , 137.7 , 136.7 , 130.6 , 130.4 , 130.4 ,

129.5 , 129.3 , 128.5 , 125.7 , 124.9 , 20.3 , 9.7 .

EA calcd. for C16H15N3: C, 77.08; H, 6.06; N, 16.85. Found: C, 76.69; H, 6.12; N, 16.56.

HRMS: calcd for C16H16N3 [M + H]+: 250.1344, found: 250.1344; calcd for C16H15N3Na

[M + Na]+: 272.1164, found: 272.1161.

5-methyl-4-(naphthalen-1-yl)-1-phenyl-1H-1,2,3-triazole (3d)

Following general procedure 3d was obtained from 4-bromo-5-methyl-1-phenyl-1H-

1,2,3-triazole and naphthalen-1-ylboronic acid. Resulting solid was purified by chromatography

to give 137 mg (96%, KOH as a base) and 124 mg (87%, NaHCO3 as a base) of 5-methyl-4-

(naphthalen-1-yl)-1-phenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.16.

1H NMR (600 MHz, Chloroform-d) δ 8.10 – 8.03 (m, 1H), 7.96 – 7.90 (m, 2H), 7.64 –

7.50 (m, 9H), 2.31 (s, 3H).


129.5 , 129.1 , 128.5 , 128.5 , 128.3 , 126.6 , 126.1 , 126.0 , 125.4 , 125.2 , 10.0.

EA calcd. for C19H15N3: C, 79.98; H, 5.30; N, 14.73. Found: C, 79.54; H. 5.29; N, 14.49.


[M + Na]+: 308.1164, found: 308.1161.

5-methyl-1-phenyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3e)

Following general procedure 3e was obtained from 4-bromo-5-methyl-1-phenyl-1H-

1,2,3-triazole and thiophen-3-ylboronic acid. Resulting solid was purified by chromatography to

give 119 mg (99%, KOH as a base) and 105 mg (87%, NaHCO3 as a base) of 5-methyl-1-

phenyl-4-(thiophen-3-yl)-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.14.

1H NMR (600 MHz, Chloroform-d) δ 7.63 – 7.46 (m, 7H), 7.43 (s, 1H), 2.47 (s, 3H).


126.7 , 126.2 , 125.3 , 121.5 , 10.2 .

EA calcd. for C13H11N3S: C, 64.70; H, 4.59; N, 17.41. Found: С, 64.39; H, 4.93; N,

16.99.

IR (υ/cm–1): 758 (vs), 789 (s), 1253 (vs), 1501 (s), 1596 (m), 2920 (s), 3054 (m).

4-(4-fluorophenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole (3f) 6a

Following general procedure 3e was obtained from 4-bromo-5-methyl-1-phenyl-1H-

1,2,3-triazole and 4-fluorophenylboronic acid. Resulting solid was purified by chromatography

to give 125 mg (99%) of 4-(4-fluorophenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.21.


7.14 (m, 2H), 2.46 (s, 3H).

13C{1H} NMR (151 MHz, Chloroform-d) δ 162.59 (d, J = 247.3 Hz), 144.17 , 136.42 ,

129.68 , 129.07 (d, J = 8.0 Hz), 127.67 (d, J = 3.1 Hz), 125.35 , 115.85 (d, J = 21.8 Hz), 10.32.

4-mesityl-5-methyl-1-phenyl-1H-1,2,3-triazole (3g)

Following general procedure 3g was obtained from mesitylboronic acid and 4-bromo-5-

methyl-1-phenyl-1H-1,2,3-triazole. Resulting solid was purified by chromatography and

recrystallization from hexane to give 260 mg (94%) of 4-mesityl-5-methyl-1-phenyl-1H-1,2,3-

triazole.

1H NMR (600 MHz, Chloroform-d) δ 7.6 – 7.5 (m, 5H), 7.0 (s, 2H), 2.3 (s, 3H), 2.2 (s,

3H), 2.1 (s, 6H).


128.3 , 127.0 , 124.8 , 21.3 , 20.4 , 9.3 .


[M + Na]+: 300.1477, found: 300.1477.

1-(4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone (3h)

Following general procedure 3h was obtained from 4-acetylphenylboronic acid and 4-

bromo-5-methyl-1-phenyl-1H-1,2,3-triazole. Resulting solid was purified by chromatography to

give 258 mg (93%) of 1-(4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone.

1H NMR (600 MHz, Chloroform-d) δ 8.07 (d, J = 7.8 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H),

7.57 (dd, J = 15.5, 6.3 Hz, 3H), 7.51 (d, J = 7.5 Hz, 2H), 2.65 (s, 3H), 2.53 (s, 3H).


129.8 , 129.0 , 127.1 , 125.5 , 26.8 , 10.6 .

HRMS: calcd for C17H16N3O [M + H]+: 278.1293, found: 278.1293; calcd for

C17H15N3ONa [M + Na]+: 300.1112, found: 300.1110.

1,4-diphenyl-5-propyl-1H-1,2,3-triazole (3i)

Following general procedure 3i was obtained from 4-chloro-1-phenyl-5-propyl-1H-1,2,3-

triazole and phenylboronic acid. Resulting solid was purified by chromatography to give 101 mg

(77%) of 1,4-diphenyl-5-propyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.13.


7.46 (m, 4H), 7.40 – 7.36 (m, 1H), 2.87 – 2.84 (m, 2H), 1.48 – 1.43 (m, 2H), 0.79 (t, J = 7.4 Hz,

3H).


128.9 , 128.0 , 127.5 , 126.0 , 25.4 , 22.0 , 13.9 .



[M + Na]+: 286.1320, found: 286.1319.

1-phenyl-5-propyl-4-p-tolyl-1H-1,2,3-triazole (3j)

Following general procedure 3j was obtained from 4-chloro-1-phenyl-5-propyl-1H-1,2,3-

triazole and p-tolylboronic acid. Resulting solid was purified by chromatography to give 137 mg

(99%) of 1-phenyl-5-propyl-4-p-tolyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.13.


– 7.45 (m, 2H), 7.28 (d, J = 8.0 Hz, 2H), 2.85 – 2.82 (m, 2H), 2.40 (s, 3H), 1.44 (h, J = 7.4 Hz,

2H), 0.78 (t, J = 7.4 Hz, 3H).

13C{1H} NMR (151 MHz, Chloroform-d) δ 144.7 , 137. 7 , 136.8 , 134.1 , 129.7 , 129.6 ,

129.5 , 128.8 , 127.3 , 125.9 , 25.3 , 21.9 , 21.4 , 13.8 .



[M + Na]+: 300.1477, found: 300.1479.

4-(naphthalen-1-yl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3k)

Following general procedure 3k was obtained from 4-chloro-1-phenyl-5-propyl-1H-

1,2,3-triazole and naphthalen-1-ylboronic acid. Resulting solid was purified by to give 94 mg

(60%) of 4-(naphthalen-1-yl)-1-phenyl-5-propyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.12.


2.69 (m, 2H), 1.24 – 1.20 (m, 2H), 0.59 (t, J = 7.4 Hz, 3H).


129.7 , 129.1 , 128.9 , 128.4 , 128.3 , 126.6 , 126.1 , 126.0 , 125.6 , 125.3 , 25.2 , 21.7 , 13.6 .

EA calcd. for C21H19N3: C, 80.48; H, 6.11; N, 13.41. Found: C, 80.53, H, 6.27; N, 13.21.


[M + Na]+: 336.1476, found: 314.1654.

4-(3-nitrophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3l)

Following general procedure 3l was obtained from 4-chloro-1-phenyl-5-propyl-1H-1,2,3-

triazole and 3-nitrophenylboronic acid. Resulting solid was purified by chromatography give 117

mg (76%) of 4-(3-nitrophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.15.

1H NMR (600 MHz, Chloroform-d) δ 8.60 (s, 1H), 8.22 – 8.18 (m, 2H), 7.65 (t, J = 8.0

Hz, 1H), 7.58 (d, J = 6.9 Hz, 3H), 7.49 – 7.46 (m, 2H), 2.91 – 2.87 (m, 2H), 1.49 (q, J = 7.6 Hz,

2H), 0.83 (t, J = 7.3 Hz, 3H).


130.2 , 129.9 , 129.8 , 126.0 , 122.6 , 121.7 , 25.4 , 22.0 , 13.8 .

EA calcd. for C17H16N4O2: C, 66.22; H 5.23; N, 18.17. Found: C, 66.55; H, 5.85, 17.76.

IR (υ/cm–1): 767 (s), 809 (m), 890 (m), 997 (m), 1103 (m), 1255 (m), 1348 (vs), 1500 (s),

1531 (s), 1560 (m), 2852 (m), 2923 (s), 2965 (m).

4-(4-fluorophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3m)

Following general procedure 3m was obtained from 4-chloro-1-phenyl-5-propyl-1H-


to give 122 mg (87%) of 4-(4-fluorophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.16.


7.44 (m, 2H), 7.19 – 7.13 (m, 2H), 2.83 – 2.80 (m, 2H), 1.45 – 1.40 (m, 2H), 0.77 (t, J = 7.4 Hz,

3H).

13C{1H} NMR (151 MHz, Chloroform-d) δ 162.6 (d, J = 247.1 Hz), 143.9 , 136.6 , 134.3

, 129.9 , 129.7 , 129.2 (d, J = 8.2 Hz), 127.8 (d, J = 3.2 Hz), 125.9 , 115.8 (d, J = 21.5 Hz), 25.3 ,

21.9 , 13.9 .

EA calcd. for C17H16FN3: C, 72.58; H, 5.73; N, 14.94. Found: C, 72.52; H, 5.70; N,

14.63.

IR (υ/cm–1): 696 (m), 769 (s), 846 (s), 991 (m), 1095 (m), 1157 (m), 1216 (s), 1249 (m),

1367 (m), 1459 (m), 1502 (vs), 1562 (w), 1596 (m), 2854 (w), 2873 (w), 2927 (m), 2965 (m),

3062 (w).

1-phenyl-5-propyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3n)

Following general procedure 3n was obtained from 4-chloro-1-phenyl-5-propyl-1H-


give 94 mg (70%) of 1-phenyl-5-propyl-4-(thiophen-3-yl)-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.13.


2.80 (m, 2H), 1.51 (dq, J = 15.0, 7.4 Hz, 2H), 0.84 (t, J = 7.4 Hz, 3H).


126.7 , 126.2 , 125.9 , 121.5 , 25.4 , 22.0 , 14.0 .

EA calcd. for C15H15N3S: C, 67.88; H, 5.61; N, 15.60. Found: C, 67.70; H, 6.00; N,

15.07.

IR (υ/cm–1): 696 (vs), 779 (vs), 796 (vs), 998 (m), 1259 (s), 1326 (m), 1413 (m), 1463 (s),

1502 (vs), 1596 (m), 2869 (m), 2927 (vs), 2956 (s), 3104 (m).

1,5-diphenyl-4-p-tolyl-1H-1,2,3-triazole (3o)

Following general procedure 3p was obtained from 4-chloro-1,5-diphenyl-1H-1,2,3-

triazole and p-tolylboronic acid. Resulting solid was purified by chromatography to give 154 mg

(99%) of 1,5-diphenyl-4-p-tolyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.15.


7.17 (m, 2H), 7.13 (d, J = 7.9 Hz, 2H), 2.34 (s, 3H).


129.3 , 129.2 , 129.1 , 129.0 , 127.9 , 127.9 , 127.3 , 125.2 , 21.4 .



[M + Na]+: 334.1320, found: 334.1320.

4-(naphthalen-1-yl)-1,5-diphenyl-1H-1,2,3-triazole (3p)

Following general procedure 3p was obtained from 4-chloro-1,5-diphenyl-1H-1,2,3-

triazole and naphthalen-1-ylboronic acid. Resulting solid was purified by chromatography to

give 172 mg (99%) of 4-(naphthalen-1-yl)-1,5-diphenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.19.


– 7.37 (m, 9H), 7.22 (d, J = 7.4 Hz, 1H), 7.16 (t, J = 7.5 Hz, 2H), 7.01 (d, J = 7.2 Hz, 2H).

13C{1H} NMR (101 MHz, Chloroform-d) δ 144.8, 136.9, 135.6, 133.9, 132.3, 129.8,

129.4, 129.2, 129.1, 129.1, 129.0, 128.8, 128.3, 128.2, 127.1, 126.5, 126.1, 126.1, 125.4, 125.3.



[M + Na]+: 370.1320, found: 370.1316.

1-benzyl-5-methyl-4-phenyl-1H-1,2,3-triazole (3q) 6a, 7

Following general procedure 3q was obtained from 1-benzyl-4-bromo-5-methyl-1H-


123 mg (99%) of 1-benzyl-5-methyl-4-phenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.20.

1H NMR (600 MHz, Chloroform-d) δ 7.70 (d, 2H), 7.44 (t, J = 7.7 Hz, 2H), 7.37 – 7.30

(m, 4H), 7.21 (d, J = 7.3 Hz, 2H), 5.55 (s, 2H), 2.33 (s, 3H). 13C{1H} NMR (151 MHz, Chloroform-d) δ 145.1 , 129.3 , 129.1 , 128.8 , 128.4 , 127.8 ,

127.2, 52.2 , 9.3 .

1-benzyl-5-methyl-4-p-tolyl-1H-1,2,3-triazole (3r)

Following general procedure 3r was obtained from p-tolylboronic acid, 1-benzyl-4-

bromo-5-methyl-1H-1,2,3-triazole (130 mg, 99%, KOH as a base) and (109 mg, 83%, NaHCO3

as a base) or from 1-benzyl-4-iodo-5-methyl-1H-1,2,3-triazole (119 mg, 90%). Resulting solid

was purified by chromatography to give 1-benzyl-5-methyl-4-p-tolyl-1H-1,2,3-triazole as white

solid.

Rf (CH2Cl2): 0.13.


(d, J = 8.0 Hz, 2H), 7.16 (d, J = 7.0 Hz, 2H), 5.48 (s, 2H), 2.34 (s, 3H), 2.26 (s, 3H). 13C{1H} NMR (151 MHz, Chloroform-d) δ 145.0 , 137.4 , 134.9 , 129.4 , 129.0 , 128.9 ,

128.8 , 128.3 , 127.2 , 127.0 , 52.0 , 21.3 , 9.2 .


1-benzyl-5-methyl-4-o-tolyl-1H-1,2,3-triazole (3s)

Following general procedure 3s was obtained from 1-benzyl-4-bromo-5-methyl-1H-

1,2,3-triazole and o-tolylboronic acid. Resulting solid was purified by chromatography to give

130 mg (99%) of 1-benzyl-5-methyl-4-o-tolyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.15.


7.25 (m, 2H), 7.23 – 7.19 (m, 4H), 5.53 (s, 2H), 2.28 (s, 3H), 2.09 (s, 3H).


130.2 , 129.0 , 128.3 , 128.3 , 127.2 , 125.6 , 52.1 , 20.2 , 8.6 .


1-benzyl-5-methyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole (3t)

Following general procedure 3t was obtained from 1-benzyl-4-bromo-5-methyl-1H-1,2,3-


give 142 mg (95%) of 1-benzyl-5-methyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.17.


7.54 – 7.46 (m, 4H), 7.43 – 7.32 (m, 3H), 7.28 (d, J = 7.1 Hz, 2H), 5.62 (s, 2H), 2.14 (s, 3H).


128.7 , 128.5 , 128.4 , 128.2 , 127.4 , 126.5 , 126.1 , 125.9 , 125.3 , 52.3 , 8.9 .

EA calcd. for C20H17N3: C, 79.98; H, 5.30; N, 14.73. C, 79.24; H. 5.29; N, 14.49.

1-benzyl-4-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole (3u)

Following general procedure 3u was obtained from 1-benzyl-4-bromo-5-methyl-1H-


to give 132 mg (99%) of 1-benzyl-4-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.22.


7.18 (m, 2H), 7.15 – 7.09 (m, 2H), 5.54 (s, 2H), 2.31 (s, 3H).

13C{1H} NMR (151 MHz, Chloroform-d) δ 162.5 (d, J = 246.9 Hz), 144.4 , 134.8 , 129.2

, 129.0 (d, J = 8.0 Hz), 128.5 , 127.3 , 115.8 (d, J = 21.7 Hz), 52.2 , 9.3 .


15.47.

IR (υ/cm–1): 732 (s), 794 (m), 840 (s), 1159 (m), 1222 (s), 1349 (m), 1507 (vs), 1567 (w).

1-benzyl-5-methyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3v)

Following general procedure 3v was obtained from 1-benzyl-4-bromo-5-methyl-1H-


give 126 mg (99%) of 1-benzyl-5-methyl-4-(thiophen-3-yl)-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.17.

1H NMR (600 MHz, Chloroform-d) δ 7.52 (dd, J = 5.0, 1.2 Hz, 1H), 7.49 (dd, J = 3.0, 1.3 Hz,

1H), 7.38 (dd, J = 5.0, 3.0 Hz, 1H), 7.32 (tdd, J = 8.5, 6.7, 3.6 Hz, 3H), 7.17 (d, J = 6.7 Hz, 2H), 5.51 (s,

2H), 2.30 (s, 3H).

13C{1H} (151 MHz, Chloroform-d) δ 141.5 , 134.9 , 129.1 , 128.4 , 127.2 , 126.0 , 121.2 ,

52.0 , 9.1.

EA calcd. for C14H13N3S: C, 65.85; H, 5.13; N, 16.46. Found: C, 65.31; H, 5.35; N,

16.39.

IR (υ/cm–1): 700 (s), 729 (vs), 787 (s), 857 (m), 1073 (m), 1181 (m), 1240 (s), 1312 (m),

3107 (m).

1-benzyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5a) 8

Following general procedure 5a was obtained from p-tolylboronic acid, 1-benzyl-5-

chloro-4-phenyl-1H-1,2,3-triazole (161 mg, 99%, KOH as a base) and (116 mg, 71%, NaHCO3

as a base), from 1-benzyl-5-bromo-4-phenyl-1H-1,2,3-triazole (151 mg, 93%) or from 1-benzyl-

5-iodo-4-phenyl-1H-1,2,3-triazole (161 mg, 99%). Resulting solid was purified by

chromatography to give 1-benzyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.18.

1H NMR (600 MHz, Chloroform-d) δ 7.57 (dd, J = 8.2, 1.4 Hz, 2H), 7.27 – 7.20 (m, 9H),

7.04 (d, J = 2.1 Hz, 3H), 5.39 (s, 2H), 2.42 (s, 3H).


130.0 , 128.8 , 128.5 , 128.2 , 127.8 , 127.6 , 126.8 , 124.8 , 52.0 , 30.5 , 29.8 , 21.6 .

1-benzyl-4,5-diphenyl-1H-1,2,3-triazole (5b) 8

Following general procedure 5b was obtained from 1-benzyl-5-chloro-4-phenyl-1H-


135 mg (87%) of 1-benzyl-4,5-diphenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.13.

1H NMR (600 MHz, Chloroform-d) δ 7.57 (dd, J = 8.1, 1.4 Hz, 2H), 7.49 (t, J = 7.5 Hz,

1H), 7.43 (t, J = 7.8 Hz, 2H), 7.28 – 7.23 (m, 6H), 7.17 – 7.14 (m, 2H), 7.04 (dd, J = 6.6, 2.7 Hz,

2H), 5.42 (s, 2H).


129.3 , 128.8 , 128.6 , 128.3 , 128.0 , 127.8 , 127.6 , 126.8 , 52.2 .

1-benzyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole (5c) 9

Following general procedure 5b was obtained from 1-benzyl-5-chloro-4-phenyl-1H-

1,2,3-triazole and naphthalen-1-ylboronic acid. Resulting solid was purified by chromatography

to give 108 mg (60%) of 1-benzyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.20.


7.52 – 7.46 (m, 4H), 7.31 – 7.28 (m, 1H), 7.21 (t, J = 8.5 Hz, 2H), 7.15 – 7.12 (m, 4H), 7.08 (t, J

= 7.5 Hz, 2H), 6.80 (d, J = 7.3 Hz, 2H), 5.39 (d, J = 15.0 Hz, 1H), 5.10 (d, J = 15.0 Hz, 1H).


130.6 , 129.3 , 128.6 , 128.5 , 128.5 , 128.2 , 127.9 , 127.8 , 127.5 , 126.8 , 126.2 , 125.5 , 125.26

, 124.7 , 52.6 .

1,4-diphenyl-5-p-tolyl-1H-1,2,3-triazole (5d)

Following general procedure 5d was obtained from p-tolylboronic acid, 5-chloro-1,4-

diphenyl-1H-1,2,3-triazole (154 mg, 99%) or from 5-bromo-1,4-diphenyl-1H-1,2,3-triazole (31

mg, 20%). Resulting solid was purified by chromatography to give 1,4-diphenyl-5-p-tolyl-1H-

1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.22.

1H NMR (600 MHz, Chloroform-d) δ 7.64 – 7.60 (m, 2H), 7.38 (dd, J = 5.1, 1.7 Hz, 3H),

7.35 – 7.28 (m, 5H), 7.15 (d, J = 7.9 Hz, 2H), 7.08 (d, J = 8.1 Hz, 2H), 2.38 (s, 3H).


129.9 , 129.2 , 129.0 , 128.6 , 128.0 , 127.5 , 125.3 , 124.7 , 21.6 .


1-phenethyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5e)

Following general procedure 5e was obtained from p-tolylboronic acid, 5-chloro-1-

phenethyl-4-phenyl-1H-1,2,3-triazole (161 mg, 95%) or from 5-bromo-1-phenethyl-4-phenyl-

1H-1,2,3-triazole (158 mg, 93%). Resulting solid was purified by chromatography to give 1-

phenethyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.13.


(dd, J = 7.3, 1.8 Hz, 2H), 6.88 (d, J = 8.0 Hz, 2H), 4.38 (t, J = 7.4 Hz, 2H), 3.18 (t, J = 7.4 Hz,

2H), 2.44 (s, 3H).


129.9 , 128.9 , 128.8 , 128.5 , 127.7 , 127.0 , 126.8 , 124.7 , 49.4 , 36.7 , 21.6 .


HRMS: calcd for C23H22N3 [M + H]+: 340.1814, found: 340.1811.

1-phenethyl-4,5-diphenyl-1H-1,2,3-triazole (5f) 10

Following general procedure 5f was obtained from 5-bromo-1-phenethyl-4-phenyl-1H-


159 mg (98%) of 1-phenethyl-4,5-diphenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.17.

1H NMR (600 MHz, Chloroform-d) δ 7.54 (dd, 2H), 7.50 – 7.47 (m, 1H), 7.43 (t, J = 7.5

Hz, 2H), 7.28 – 7.21 (m, 6H), 7.02 – 6.98 (m, 2H), 6.95 (dd, J = 6.9, 2.4 Hz, 2H), 4.39 (t, 2H),

3.18 (t, J = 7.4 Hz, 2H).


129.3 , 128.9 , 128.8 , 128.5 , 127.7 , 127.0 , 126.8 , 49.5 , 36.7 .

1-methyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5g)

Following general procedure 5g was obtained from p-tolylboronic acid, 5-chloro-1-

methyl-4-phenyl-1H-1,2,3-triazole (123 g, 99%, NaHCO3 as a base) and (103 mg, 83%, KOH as

a base) or from 5-bromo-1-methyl-4-phenyl-1H-1,2,3-triazole (84 mg, 67%). Resulting solid was

purified by chromatography to give 1-methyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole as white

solid.

Rf (CH2Cl2): 0.10.


7.25 (dd, J = 14.1, 6.8 Hz, 3H), 7.21 (d, J = 8.1 Hz, 2H), 3.92 (s, 3H), 2.44 (s, 3H).


127.7 , 126.9 , 124.9 , 35.4, 21.5 .



[M + Na]+: 272.1164, found: 272.1163.

1-methyl-4,5-diphenyl-1H-1,2,3-triazole (5h) 11

Following general procedure 5р was obtained from 5-chloro-1-methyl-4-phenyl-1H-


116 mg (99%) of 1-methyl-4,5-diphenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.11.


7.34 (m, 2H), 7.30 – 7.26 (m, 3H), 3.94 (s, 3H).

13C{1H} NMR (151 MHz, Chloroform-d) δ 144.42 , 134.20 , 131.02 , 129.95 , 129.82 ,

128.58 , 127.97 , 127.85 , 126.99 , 35.45 .

1-methyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole (5i)

Following general procedure 5i was obtained from 5-chloro-1-methyl-4-phenyl-1H-1,2,3-


give 141 mg (99%) of 1-methyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.11.


7.58 (dt, J = 22.7, 7.2 Hz, 2H), 7.52 – 7.44 (m, 4H), 7.38 (d, J = 8.4 Hz, 1H), 7.19 – 7.13 (m,

3H), 3.76 (s, 3H).


129.0 , 128.9 , 128.6 , 127.8 , 127.0 , 126.3 , 125.8 , 125.5 , 124.7 , 35.2 .

EA calcd. for C19H15N3: C, 79.98; H, 5.30; N, 14.73. Найдено: C, 79.08; H, 5.34; N,

14.67.

HRMS: calcd for C19H16N3 [M + H]+: 286.1344, found: 286.1340.

1-methyl-5-(3-nitrophenyl)-4-phenyl-1H-1,2,3-triazole (5j)

Following general procedure 5j was obtained from 5-chloro-1-methyl-4-phenyl-1H-1,2,3-

triazole and 3-nitrophenylboronic acid. Resulting solid was purified by chromatography to give

121 mg (86%) of 1-methyl-5-(3-nitrophenyl)-4-phenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2):0.13.

1H NMR (600 MHz, Chloroform-d) δ 8.38 (d, J = 8.1 Hz, 1H), 8.26 (s, 1H), 7.72 (t, J =

7.9 Hz, 1H), 7.68 (d, J = 7.6 Hz, 1H), 7.48 (dd, J = 6.5, 3.0 Hz, 2H), 7.32 – 7.28 (m, 3H), 3.99

(s, 3H).


127.2 , 124.8 , 124.8 , 22.8 .

EA calcd. for C15H12N4O2: C, 64.28; H, 4.32; N, 19.99. Found: C, 64.31; H, 4.51; N,

19.68.

5-(4-fluorophenyl)-1-methyl-4-phenyl-1H-1,2,3-triazole (5k)

Following general procedure 5k was obtained from 5-chloro-1-methyl-4-phenyl-1H-


to give 119 mg (94%) of 5-(4-fluorophenyl)-1-methyl-4-phenyl-1H-1,2,3-triazole as white solid.

Rf (CH2Cl2): 0.10.


7.26 (m, 3H), 7.24 – 7.20 (m, 2H), 3.92 (s, 3H).

13C NMR (151 MHz, Chloroform-d) δ 163.53 (d, J = 250.7 Hz), 144.61 , 133.18 , 131.95

(d, J = 7.9 Hz), 130.85 , 128.65 , 127.97 , 126.95 , 123.90 (d, J = 4.1 Hz), 116.82 (d, J = 21.9

Hz), 35.43 .


16.22.

HRMS: calcd for C15H13FN3 [M + H]+: 254.1094, found: 254.1091; calcd for

C15H12FN3Na [M + Na]+: 276.0912, found: 276.0908.

5-p-tolyl-4-(p-tolyloxymethyl)-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole (5l)

Following general procedure 5l was obtained from p-tolylboronic acid and 5-bromo-4-(p-

tolyloxymethyl)-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole. Resulting solid was purified by

chromatography and recrystallization from ethanol to give 173 mg (82%) of 5-p-tolyl-4-(p-

tolyloxymethyl)-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole.

1H NMR (600 MHz, Chloroform-d) δ 7.72 (s, 1H), 7.67 (d, J = 7.6 Hz, 1H), 7.52 (t, J =

7.8 Hz, 1H), 7.47 (d, J = 7.8 Hz, 1H), 7.21 – 7.15 (m, 4H), 7.10 (d, J = 8.0 Hz, 2H), 6.95 (d, J =

8.2 Hz, 2H), 5.12 (s, 2H), 2.37 (s, 3H), 2.30 (s, 3H).


130.7 , 130.1 , 130.0 , 129.9 , 129.6 , 128.0 , 125.8 , 123.2 (q, J = 272.8 Hz), 122.1 , 115.0 , 61.3

, 21.5 , 20.6 .

HRMS: calcd for C24H21F3N3O [M + H]+: 424.1637, found: 424.1632; calcd for

C24H20F3N3ONa [M + Na]+: 446.1456, found: 446.1449.

NMR spectra

Figure S1. 1H NMR (600 MHz, Chloroform-d) of 5-methyl-1-phenyl-4-p-tolyl-1H-1,2,3-triazole (3a).

Figure S2. 13C{1H} NMR (151 MHz, Chloroform-d) of 5-methyl-1-phenyl-4-p-tolyl-1H-1,2,3-triazole (3a).

Figure S3. 1H NMR (600 MHz, Chloroform-d) of 5-methyl-1,4-diphenyl-1H-1,2,3-triazole (3b).

Figure S4. 13C{1H} NMR (151 MHz, Chloroform-d) of 5-methyl-1,4-diphenyl-1H-1,2,3-triazole (3b).

Figure S5. 1H NMR (600 MHz, Chloroform-d) of 5-methyl-1-phenyl-4-o-tolyl-1H-1,2,3-triazole (3c).

Figure S6. 13C{1H} NMR (151 MHz, Chloroform-d) of 5-methyl-1-phenyl-4-o-tolyl-1H-1,2,3-triazole (3c).

Figure S7. 1H NMR (600 MHz, Chloroform-d) of 5-methyl-4-(naphthalen-1-yl)-1-phenyl-1H-1,2,3-triazole (3d).

Figure S8. 13C{1H} NMR (151 MHz, Chloroform-d) of 5-methyl-4-(naphthalen-1-yl)-1-phenyl-1H-1,2,3-triazole (3d).

Figure S9. 1H NMR (600 MHz, Chloroform-d) of 5-methyl-1-phenyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3e).

Figure S10. 13C{1H} NMR (151 MHz, Chloroform-d) of 5-methyl-1-phenyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3e).

Figure S11. 1H NMR (600 MHz, Chloroform-d) of 4-(4-fluorophenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole (3f).

Figure S12. 13C{1H} NMR (151 MHz, Chloroform-d) of 4-(4-fluorophenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole (3f).

Figure S13. 1H NMR (600 MHz, Chloroform-d) of 4-mesityl-5-methyl-1-phenyl-1H-1,2,3-triazole (3g).

Figure S14. 13C{1H} NMR (151 MHz, Chloroform-d) of 4-mesityl-5-methyl-1-phenyl-1H-1,2,3-triazole (3g).

Figure S15. 1H NMR (600 MHz, Chloroform-d) of 1-(4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone (3h).

Figure S16. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-(4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone (3h).

Figure S17. 1H NMR (600 MHz, Chloroform-d) of 1,4-diphenyl-5-propyl-1H-1,2,3-triazole (3i).

Figure S18. 13C{1H} NMR (151 MHz, Chloroform-d) of 1,4-diphenyl-5-propyl-1H-1,2,3-triazole (3i).

Figure S19. 1H NMR (600 MHz, Chloroform-d) of 1-phenyl-5-propyl-4-p-tolyl-1H-1,2,3-triazole (3j).

Figure S20. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-phenyl-5-propyl-4-p-tolyl-1H-1,2,3-triazole (3j).

Figure S21. 1H NMR (600 MHz, Chloroform-d) of 4-(naphthalen-1-yl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3k).

Figure S22. 13C{1H} NMR (151 MHz, Chloroform-d) of 4-(naphthalen-1-yl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3k).

Figure S23. 1H NMR (600 MHz, Chloroform-d) of 4-(3-nitrophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3l).

Figure S24. 13C{1H} NMR (151 MHz, Chloroform-d) of 4-(3-nitrophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3l).

Figure S25. 1H NMR (600 MHz, Chloroform-d) of 4-(4-fluorophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3m).

Figure S26. 13C{1H} NMR (151 MHz, Chloroform-d) of 4-(4-fluorophenyl)-1-phenyl-5-propyl-1H-1,2,3-triazole (3m).

Figure S27. 1H NMR (600 MHz, Chloroform-d) of 1-phenyl-5-propyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3n).

Figure S28. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-phenyl-5-propyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3n).

Figure S29. 1H NMR (600 MHz, Chloroform-d) of 1,5-diphenyl-4-p-tolyl-1H-1,2,3-triazole (3o).

Figure S30. 13C{1H} NMR (151 MHz, Chloroform-d) of 1,5-diphenyl-4-p-tolyl-1H-1,2,3-triazole (3o).

Figure S31. 1H NMR (600 MHz, Chloroform-d) of 4-(naphthalen-1-yl)-1,5-diphenyl-1H-1,2,3-triazole (3p).

Figure S32. 13C{1H} NMR (151 MHz, Chloroform-d) of 4-(naphthalen-1-yl)-1,5-diphenyl-1H-1,2,3-triazole (3p).

Figure S33. 1H NMR (600 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-phenyl-1H-1,2,3-triazole (3q).

Figure S34. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-phenyl-1H-1,2,3-triazole (3q).

Figure S35. 1H NMR (600 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-p-tolyl-1H-1,2,3-triazole (3r).

Figure S36. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-p-tolyl-1H-1,2,3-triazole (3r).

Figure S37. 1H NMR (600 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-o-tolyl-1H-1,2,3-triazole (3s).

Figure S38. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-o-tolyl-1H-1,2,3-triazole (3s).

Figure S39. 1H NMR (600 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole (3t).

Figure S40. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole (3t).

Figure S41. 1H NMR (600 MHz, Chloroform-d) of 1-benzyl-4-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole (3u).

Figure S42. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-benzyl-4-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole (3u).

Figure S43. 1H NMR (600 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3v).

Figure S44. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-benzyl-5-methyl-4-(thiophen-3-yl)-1H-1,2,3-triazole (3v).

Figure S45. 1H NMR (600 MHz, Chloroform-d) of 1-benzyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5a).

Figure S46. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-benzyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5a).

Figure S47. 1H NMR (600 MHz, Chloroform-d) of 1-benzyl-4,5-diphenyl-1H-1,2,3-triazole (5b).

Figure S48. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-benzyl-4,5-diphenyl-1H-1,2,3-triazole (5b).

Figure S49. 1H NMR (600 MHz, Chloroform-d) of 1-benzyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole (5c).

Figure S50. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-benzyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole (5c).

Figure S51. 1H NMR (600 MHz, Chloroform-d) of 1,4-diphenyl-5-p-tolyl-1H-1,2,3-triazole (5d).

Figure S52. 13C{1H} NMR (151 MHz, Chloroform-d) of 1,4-diphenyl-5-p-tolyl-1H-1,2,3-triazole (5d).

Figure S53. 1H NMR (600 MHz, Chloroform-d) of 1-phenethyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5e).

Figure S54. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-phenethyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5e).

Figure S55. 1H NMR (600 MHz, Chloroform-d) of 1-phenethyl-4,5-diphenyl-1H-1,2,3-triazole (5f).

Figure S56. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-phenethyl-4,5-diphenyl-1H-1,2,3-triazole (5f).

Figure S57. 1H NMR (600 MHz, Chloroform-d) of 1-methyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5g).

Figure S58. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-methyl-4-phenyl-5-p-tolyl-1H-1,2,3-triazole (5g).

Figure S59. 1H NMR (600 MHz, Chloroform-d) of 1-methyl-4,5-diphenyl-1H-1,2,3-triazole (5h).

Figure S60. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-methyl-4,5-diphenyl-1H-1,2,3-triazole (5h).

Figure S61. 1H NMR (600 MHz, Chloroform-d) of 1-methyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole (5i).

Figure S62. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-methyl-5-(naphthalen-1-yl)-4-phenyl-1H-1,2,3-triazole (5i).

Figure S63. 1H NMR (600 MHz, Chloroform-d) of 1-methyl-5-(3-nitrophenyl)-4-phenyl-1H-1,2,3-triazole (5j).

Figure S64. 13C{1H} NMR (151 MHz, Chloroform-d) of 1-methyl-5-(3-nitrophenyl)-4-phenyl-1H-1,2,3-triazole (5j).

Figure S65. 1H NMR (600 MHz, Chloroform-d) of 5-(4-fluorophenyl)-1-methyl-4-phenyl-1H-1,2,3-triazole (5k).

Figure S66. 13C{1H} NMR (151 MHz, Chloroform-d) of 5-(4-fluorophenyl)-1-methyl-4-phenyl-1H-1,2,3-triazole (5k).

Figure S67. 1H NMR (600 MHz, Chloroform-d) of 5-p-tolyl-4-(p-tolyloxymethyl)-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole (5l).

Figure S68. 13C{1H} NMR (151 MHz, Chloroform-d) of 5-p-tolyl-4-(p-tolyloxymethyl)-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole (5l).

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Supporting Information for: General method of Suzuki Myiaura … · Supporting Information for: General method of Suzuki-Myiaura cross-coupling of 4-and 5-halo- 1,2,3-triazoles in