Supporting Information

ynthesis of ubstituted Benzothiazoles via Copper-Catalyzed Condensation of 2-Aminobenzenethiols with itriles Yadong un,, Huanfeng Jiang,*, Wanqing Wu, Wei Zeng, Xia Wu chool of Chemistry and Chemical Engineering, outh China University of Technology, Guangzhou 510640, China College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China E-mail: jianghf@scut.edu.cn; Fax and Tel.: (+86) 20-87112906 upporting Information List of Contents A. General method...2 B. General procedure for the synthesis of products...2 C. Analytical data for 3a-3x, 4 and 5...2 D. References...7 E. MR pectra...9 1

A. General method Melting points were measured with a melting point instrument and were uncorrected. 1 H MR and 13 C MR spectra were recorded on Bruker Avance (400 and 100 MHz, respectively) instrument internally referenced to tetramethylsilane (TM), chloroform or dimethylsulfoxide signals. IR spectra were obtained either as potassium bromide pellets or as liquid films between two potassium bromide pellets with a Bruker Vector 22 spectrometer. GC-M was obtained using electron ionization (EI). High-resolution mass spectra were obtained with a LCM-IT-TOF mass spectrometer. TLC was performed by using commercially prepared 100 400 mesh silica gel plates (GF 254 ) and visualization was effected at 254 nm. All reagents were obtained from commercial suppliers and used without further purification. B. General procedure for the synthesis of products ubstituted 2-aminobenzenethiol (0.5 mmol), nitrile (0.5 mmol), Cu(OAc) 2 (10 mol %), Et 3 (0.5 mmol) and ethanol (2.5 ml) were added to a tube equipped with magnetic stirrer bar. The mixture was stirred at 70 C (oil bath temperature) for 6h. After the reaction was finished (monitored by TLC), the mixture was cooled to room temperature and quenched with aqueous a 2 CO 3, and the crude product was extracted with ethyl acetate. The organic extracts were concentrated in vacuum, and the resulting residue was purified by column chromatography on silica gel with petroleum ether/ethyl acetate as eluent to afford the desired product. C. Analytical data for 3a-3x, 4 and 5 2-Phenylbenzo[d]thiazole (3a) 1 White solid (91 mg, 86%). IR (KBr): 1477, 1433, 1313, 1224, 963, 763, 688. 1 H MR (400 MHz, CDCl 3 ) δ 8.10 8.07 (m, 3H), 7.90 (d, J = 8.0 Hz, 1H), 7.51 7.47 (m, 4H), 7.38 (t, J = 7.6 Hz, 1H). 13 C MR (100 MHz, CDCl 3 ) δ 168.1, 154.1, 135.1, 133.6, 130.9, 129.0, 127.6, 126.3, 125.2, 123.2, 121.6. M (EI) m/z: 211, 184, 149, 108, 82, 69, 58. 2

2-p-Tolylbenzo[d]thiazole (3b) 1 CH 3 White solid (98 mg, 87%). IR (KBr):1481, 1433, 1312, 961, 818, 759, 728, 484. 1 H MR (400 MHz, CDCl 3 ) δ 8.05 (d, J = 8.1 Hz, 1H), 7.98 (d, J = 8.1 Hz, 2H), 7.88 (d, J = 7.9 Hz, 1H), 7.47 (t, J = 7.6 Hz, 1H), 7.36 (t, J = 7.5 Hz, 1H), 7.29 (d, J = 8.0 Hz, 2H), 2.41 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 168.2, 154.1, 141.4, 134.9, 130.9, 129.7, 127.5, 126.2, 125.0, 123.0, 121.5, 21.5.M (EI) m/z: 225, 210, 116, 113, 91, 82, 69. 2-(4-Methoxyphenyl)benzo[d]thiazole (3c) 1 OCH 3 White solid (100 mg, 83%). IR (KBr): 1603, 1412, 1310, 1258, 1025, 966, 859, 757, 552, 508, 436. 1 H MR (400 MHz, CDCl 3 ) δ 8.02 (d, J = 8.8 Hz, 3H), 7.86 (d, J = 7.9 Hz, 1H), 7.46 (t, J = 7.1 Hz, 1H), 7.34 (t, J = 7.6 Hz, 1H), 6.99 (d, J = 8.8 Hz, 2H), 3.86 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 167.9, 161.9, 154.2, 134.8, 129.1, 126.4, 126.2, 124.8, 122.8, 121.5, 114.3, 55.4. M (EI) m/z: 241, 226, 198, 154, 121, 108, 82, 69. 2-(4-isopropylphenyl)benzo[d]thiazole (3d) 2 White solid (114 mg, 90%). IR (KBr): 2959, 1483, 1412, 1311, 1226, 967, 840, 756, 726, 437. 1 H MR (400 MHz, CDCl 3 ) δ 8.05 (d, J = 8.1 Hz, 1H), 8.00 (d, J = 8.3 Hz, 2H), 7.85 (d, J = 7.9 Hz, 1H), 7.48 7.44 (m, 1H), 7.36 7.31 (m, 3H), 3.00 2.90 (m, 1H), 1.28 (d, J = 6.9 Hz, 6H). 13 C MR (100 MHz, CDCl 3 ) δ 168.1, 154.2, 152.2, 134.9, 131.3, 127.6, 127.1, 126.2, 124.9, 123.0, 121.5, 34.1, 23.7. M (EI) m/z: 253, 238, 223, 210, 108, 82, 69. 4-(Benzo[d]thiazol-2-yl)-,-dimethylbenzenamine (3e) 3 (CH 3 ) 2 White solid (117 mg, 92%). IR (KBr): 1476, 1434, 1314, 1226, 1062, 962, 816, 751, 720, 431. 1 H MR (400 MHz, CDCl 3 ) δ 7.97 (t, J = 8.7 Hz, 3H), 7.83 (d, J = 7.9 Hz, 1H), 7.43 (t, J = 7.7 Hz, 1H), 7.30 (t, J = 7.6 Hz, 1H), 6.74 (d, J = 8.9 Hz, 2H), 3.05 (s, 6H). 13 C MR (100 MHz, CDCl 3 ) δ 168.8, 154.4, 152.2, 134.5, 128.9, 126.0, 124.2, 122.3, 121.4, 121.3, 111.7, 40.1. M (EI) m/z: 254, 238, 223, 210, 109, 69. 2-(4-(Trifluoromethyl)phenyl)benzo[d]thiazole (3f) 4 CF 3 White solid (105 mg, 75%). IR (KBr): 1483, 1434, 1323, 1110, 970, 839, 760, 620, 439. 1 H MR (400 MHz, CDCl 3 ) δ 8.19 (d, J = 8.1 Hz, 2H), 8.10 (d, J = 8.1 Hz, 1H), 7.91 (d, J = 8.0 Hz, 1H), 7.74 (d, J = 8.2 Hz, 2H), 7.54 7.50 (m, 1H), 7.44 7.40 (m, 1H). 13 C MR (100 MHz, CDCl 3 ) δ 166.0, 154.0, 136.7, 135.2, 132.4 (q, J = 32.6 Hz), 127.7, 126.6, 125.9 (q, J = 3.6 Hz), 123.8 (q, J = 270.7 Hz), 123.6, 121.7. M (EI) m/z: 279, 260, 210, 139, 114, 108, 82, 69. 4-(Benzo[d]thiazol-2-yl)benzonitrile (3g) 5 C White solid (91 mg, 77%). IR (KBr): 1769, 1479, 1247, 1054, 966, 838, 762, 728, 555, 446. 1 H MR (400 MHz, DMO) δ 8.28 (d, J = 8.4 Hz, 2H), 8.21 (d, J = 8.0 Hz, 1H), 8.13 (d, J = 8.1 Hz, 1H), 8.04 (d, J = 8.4 Hz, 2H), 7.62 3

7.58 (m, 1H), 7.53 (t, J = 7.6 Hz, 1H). 13 C MR (100 MHz, DMO) δ 165.3, 153.4, 136.7, 134.9, 133.3, 127.8, 127.0, 126.2, 123.3, 122.6, 118.3, 113.3. M (EI) m/z: 236, 208, 175, 128, 108, 74, 69. 2-(4-Fuorophenyl)benzo[d]thiazole (3h) 1 F White solid (92 mg, 80%). IR (KBr): 1710, 1520, 1362, 1226, 1092, 967, 837, 756, 728, 499. 1 H MR (400 MHz, CDCl 3 ) δ 8.08 8.04 (m, 3H), 7.87 (d, J = 7.9 Hz, 1H), 7.48 (t, J = 7.7 Hz, 1H), 7.37 (t, J = 7.6 Hz, 1H), 7.16 (t, J = 7.7 Hz, 2H). 13 C MR (100 MHz, CDCl 3 ) δ 166.7, 164.4(d, J = 125.2 Hz,), 154.1, 135.0, 129.9 (d, J = 3.4 Hz,), 129.5(d, J = 3.8 Hz), 126.4, 125.2, 123.2, 121.6, 116.1(d, J = 22.0 Hz). M (EI) m/z: 229, 202, 185, 139, 114, 108, 82, 69. 2-(4-Chlorophenyl)benzo[d]thiazole (3i) 1 Cl White solid (101 mg, 82%). IR (KBr): 1473, 1433, 1313, 1249, 966, 826, 756, 729, 481. 1 H MR (400 MHz, CDCl 3 ) δ 8.06 (d, J = 8.2 Hz, 1H), 8.01 (d, J = 8.5 Hz, 2H), 7.88 (d, J = 8.0 Hz, 1H), 7.52 7.36 (m, 4H). 13 C MR (100 MHz, CDCl 3 ) δ 166.6, 154.0, 137.0, 135.0, 132.1, 129.2, 128.7, 126.5, 125.4, 123.3, 121.6. M (EI) m/z: 245, 218, 183, 137, 108, 82, 69. 2-(4-Bromophenyl)benzo[d]thiazole (3j) 1 Br White solid (135 mg, 93%). IR (KBr): 1503, 1392, 1311, 1224, 968, 820, 754, 722, 477. 1 H MR (400 MHz, CDCl 3 ) δ 8.06 (d, J = 8.2 Hz, 1H), 7.94 (d, J = 8.4 Hz, 2H), 7.89 (d, J = 7.9 Hz, 1H), 7.61 (d, J = 8.4 Hz, 2H), 7.49 (t, J = 7.7 Hz, 1H), 7.39 (t, J = 7.6 Hz, 1H). 13 C MR (100 MHz, CDCl 3 ) δ 166.7, 154.0, 135.0, 132.5, 132.2, 128.9, 126.5, 125.4, 125.4, 123.3, 121.6. M (EI) m/z: 289, 291, 210, 183, 177, 144, 108, 69. 2-(4-Iodophenyl)benzo[d]thiazole (3k) 6 I White solid (148 mg, 88%). IR (KBr): 1498, 1388, 1310, 1248, 967, 816, 754, 723, 474. 1 H MR (400 MHz, CDCl 3 ) δ 8.06 (d, J = 8.1 Hz, 1H), 7.88 (d, J = 8.0 Hz, 1H), 7.83 7.78 (m, 4H), 7.49 (t, J = 7.6 Hz, 1H), 7.38 (t, J = 7.5 Hz, 1H). 13 C MR (100 MHz, CDCl 3 ) δ 166.8, 154.0, 138.1, 135.0, 133.0, 128.9, 126.5, 125.4, 123.3, 121.6, 97.5. M (EI) m/z: 337, 281, 253, 207, 191, 147, 108, 91, 73. Br 2-(3-Bromo-4-methylphenyl)benzo[d]thiazole (3l) White solid (135 mg, 89%), MP = 115-117 o C. IR (KBr): 1472, CH 1433, 1375, 1310, 1284, 973, 824, 756, 724, 433. 1 3 H MR (400 MHz, CDCl 3 ) δ 8.29 (d, J = 1.4 Hz, 1H), 8.07 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 7.9 Hz, 2H), 7.50 (t, J = 7.7 Hz, 1H), 7.39 (t, J = 7.3 Hz, 1H), 7.34 (d, J = 7.9 Hz, 1H), 2.47 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 166.3, 154.0, 141.0, 135.0, 132.9, 131.2, 131.0, 126.4, 126.3, 125.5, 125.3, 123.2, 121.6, 23.0. M (EI) m/z: 303, 305, 224, 209, 191, 160, 152, 108, 82, 63. HRM EI (m/z): calcd for C 14 H 10 Br [M+H] +, 303.9790; found 303.9785. 4

2-(aphthalen-3-yl)benzo[d]thiazole (3m) 7 White solid (105 mg, 80%). IR (KBr): 1496, 1453, 1361, 1311, 981, 934, 852, 829, 747, 728, 476. 1 H MR (400 MHz, CDCl 3 ) δ 8.55 (s, 1H), 8.20 (d, J = 8.6 Hz, 1H), 8.11 (d, J = 8.1 Hz, 1H), 7.96 7.85 (m, 4H), 7.54 7.48 (m, 3H), 7.38 (t, J = 7.5 Hz, 1H). 13 C MR (100 MHz, CDCl 3 ) δ 168.1, 154.2, 135.1, 134.6, 133.2, 130.9, 128.8, 128.8, 127.8, 127.6, 127.4, 126.9, 126.4, 125.2, 124.4, 123.2, 121.6. M (EI) m/z: 261, 209, 189, 153, 131, 114, 82, 66. 2-(Furan-2-yl)benzo[d]thiazole (3n) 1 White solid (91 mg, 90%). IR (KBr): 1505, 1433, 1245, 1153, 1012, 896, 745, 590, 436. 1 H MR (400 MHz, CDCl 3 ) δ 8.05 (d, J = 8.1 Hz, 1H), 7.88 (d, J = 7.9 Hz, 1H), 7.60 (s, 1H), 7.48 (t, J = 8.1 Hz, 1H), 7.37 (t, J = 7.6 Hz, 1H), 7.19 (d, J = 3.2 Hz, 1H), 6.59 (dd, J = 3.4, 1.7 Hz, 1H). 13 C MR (100 MHz, CDCl 3 ) δ 157.5, 153.7, 148.7, 144.7, 134.3, 126.5, 125.2, 123.1, 121.5, 112.5, 111.4. M (EI) m/z: 201, 173, 146, 108, 100, 69. Cl O 5-Chloro-2-phenylbenzo[d]thiazole (3o) 1 White solid (112 mg, 91%). IR (KBr): 1475, 1433, 1262, 1221, 1069, 966, 882, 806, 762, 687, 627, 470. 1 H MR (400 MHz, CDCl 3 ) δ 8.07 8.05 (m, 3H), 7.78 (d, J = 8.5 Hz, 1H), 7.50 7.48 (m, 3H), 7.34 (dd, J = 8.5, 1.9 Hz, 1H). 13 C MR (100 MHz, CDCl 3 ) δ 169.9, 154.9, 133.3, 133.2, 132.3, 131.3, 129.1, 127.6, 125.6, 123.0, 122.3. M (EI) m/z: 245, 218, 142, 107, 91, 77. CH 3 2-Methylbenzo[d]thiazole (3p) 1 Yellow liquid (69 mg, 93%). IR (KBr): 3062, 2923, 1527, 1433, 1309, 1241, 1173, 1065, 865, 759, 729, 604, 429. 1 H MR (400 MHz, CDCl 3 ) δ 7.95 7.92 (m, 1H), 7.77 7.73 (m, 1H), 7.42 7.36 (m, 1H), 7.29 7.24 (m, 1H), 2.77 2.75 (m, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 166.5, 153.1, 135.4, 125.6, 124.4, 122.1, 121.1, 19.7. M (EI) m/z: 149, 117, 108, 104, 82, 69. 2-Cyclopropylbenzo[d]thiazole (3q) 8 Yellow liquid (79 mg, 90%). IR (KBr): 3061, 3007, 1521, 1433, 1243, 1193, 1109, 1048, 814, 758, 437. 1 H MR (400 MHz, CDCl 3 ) δ 7.89 (d, J = 8.1 Hz, 1H), 7.77 (d, J = 7.9 Hz, 1H), 7.41 (t, J = 8.1 Hz, 1H), 7.29 (t, J = 7.6 Hz, 1H), 2.42 2.35 (m, 1H), 1.21 (d, J = 6.5 Hz, 4H). 13 C MR (100 MHz, CDCl 3 ) δ 174.4, 153.3, 134.1, 125.8, 124.2, 122.0, 121.3, 15.2, 11.6. M (EI) m/z: 175, 149, 135, 108, 69. 2-Benzylbenzo[d]thiazole (3r) 9 Yellow liquid (95 mg, 84%). IR (KBr): 3062, 3029, 1647, 1517, 1435, 1311, 1112, 889, 760, 704, 430. 1 H MR (400 MHz, CDCl 3 ) δ 7.99 (d, J = 8.1 Hz, 1H), 7.75 (d, J = 8.0 Hz, 1H), 7.42 (t, J = 7.7 Hz, 1H), 7.36 7.22 (m, 6H), 4.41 (s, 2H). 13 C MR (100 MHz, CDCl 3 ) δ 171.1, 153.2, 137.1, 135.6, 129.1, 128.8, 127.2, 125.9, 124.7, 122.7, 121.4, 40.5. M (EI) m/z: 225, 197, 165, 148, 111, 91, 65. 5

OCH 2-(3-Methoxybenzyl)benzo[d]thiazole (3s) 10 3 Yellow liquid (110 mg, 86%). IR (KBr): 3059, 2938, 1599, 1489, 1434, 1259, 1151, 1046, 760, 431. 1 H MR (400 MHz, CDCl 3 ) δ 7.99 (d, J = 8.2 Hz, 1H), 7.74 (d, J = 7.6 Hz, 1H), 7.41 (t, J = 7.7 Hz, 1H), 7.31 7.22 (m, 2H), 6.93 (d, J = 7.6 Hz, 1H), 6.90 (s, 1H), 6.81 (dd, J = 8.2, 2.2 Hz, 1H), 4.38 (s, 2H), 3.75 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 170.8, 159.8, 153.1, 138.5, 135.5, 129.7, 125.8, 124.7, 122.6, 121.4, 121.3, 114.7, 112.6, 55.0, 40.5. M (EI) m/z: 255, 240, 225, 212, 159, 148, 121, 91, 69. 2-((Pyridin-2-yl)methyl)benzo[d]thiazole (3t) 11 Yellow solid (107 mg, 95%). IR (KBr): 3058, 1589, 1512, 1433, 1312, 1240, 757, 729, 430. 1 H MR (400 MHz, CDCl 3 ) δ 8.61 (d, J = 4.7 Hz, 1H), 8.00 (d, J = 8.2 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.64 (t, J = 7.7 Hz, 1H), 7.44 (t, J = 7.7 Hz, 1H), 7.36 7.31 (m, 2H), 7.20 7.17 (m, 1H), 4.64 (s, 2H). 13 C MR (100 MHz, CDCl 3 ) δ 168.6, 156.9, 153.1, 149.6, 136.9, 135.8, 125.9, 124.8, 123.5, 122.8, 122.2, 121.4, 43.1. M (EI) m/z: 225, 193, 148, 112, 78. 2-((Thiophen-3-yl)methyl)benzo[d]thiazole (3u) Brown oil (112 mg, 97%). IR (KBr): 3062, 2910, 1636, 1512, 1455, 1268, 1113, 940, 760, 727, 429. 1 H MR (400 MHz, CDCl 3 ) δ 7.99 (d, J = 8.2 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H), 7.45 (t, J = 7.7 Hz, 1H), 7.35 7.29 (m, 2H), 7.22 (s, 1H), 7.07 (d, J = 4.9 Hz, 1H), 4.46 (s, 2H). 13 C MR (100 MHz, CDCl 3 ) δ 170.6, 153.2, 136.9, 135.5, 128.3, 126.3, 126.0, 124.8, 123.0, 122.7, 121.5, 35.1. M (EI) m/z: 231, 198, 186, 173, 135, 97, 69. HRM EI (m/z): calcd for C 12 H 9 2 [M+H] +, 232.0249; found 232.0257. 2-(2-Methoxyethyl)benzo[d]thiazole (3v) OCH 3 Yellow liquid (92 mg, 95%). IR (KBr): 3061, 2925, 2827, 1693, 1517, 1436, 1114, 761, 730, 430. 1 H MR (400 MHz, CDCl 3 ) δ 7.98 (d, J = 8.1 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.45 (t, J = 7.7 Hz, 1H), 7.35 (t, J = 7.6 Hz, 1H), 3.86 3.83 (m, 2H), 3.45 3.31 (m, 5H). 13 C MR (100 MHz, CDCl 3 ) δ 168.8, 152.9, 135.3, 125.8, 124.7, 122.6, 121.4, 70.8, 58.8, 34.7. M (EI) m/z: 193, 178, 163, 150, 121, 108, 69. HRM EI (m/z): calcd for C 10 H 11 O [M+H] +, 194.0634; found 194.0621. 2-(3-Phenylpropyl)benzo[d]thiazole (3w) 12 Yellow liquid (113 mg, 89%). IR (KBr): 3026, 2989, 2857, 1519, 1435, 1109, 759, 729, 700. 1 H MR (400 MHz, CDCl 3 ) δ 7.97 (d, J = 8.1 Hz, 1H), 7.83 (d, J = 7.9 Hz, 1H), 7.45 (t, J = 7.7 Hz, 1H), 7.36 7.27 (m, 3H), 7.22 7.18 (m, 3H), 3.14 (t, J = 7.6 Hz, 2H), 2.76 (t, J = 7.6 Hz, 2H), 2.26 2.18 (m, 2H). 13 C MR (101 MHz, CDCl 3 ) δ 171.7, 153.2, 141.3, 135.1, 128.5, 128.4, 126.0, 125.9, 124.7, 122.5, 121.5, 35.2, 33.7, 31.1. M (EI) m/z: 253, 162, 149, 125, 108, 91, 78. 2-Undecylbenzo[d]thiazole (3x) 13 Yellow liquid (119 mg, 82%). IR (KBr):2924, 2853, 1521, 1436, 1310, 1239, 758, 727. 1 H MR (400 MHz, CDCl 3 ) δ 7.97 (d, J = 8.1 Hz, 1H), 7.84 (d, J = 7.9 Hz, 1H), 7.45 (t, J = 7.7 Hz, 1H), 7.34 (t, 6

J = 7.6 Hz, 1H), 3.11 (t, J = 7.7 Hz, 2H), 1.91 1.84 (m, 2H), 1.41 1.26 (m, 16H), 0.88 (t, J = 6.8 Hz, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 172.5, 153.1, 135.1, 125.9, 124.6, 122.5, 121.5, 34.3, 31.9, 29.7, 29.6, 29.6, 29.4, 29.3, 29.3, 29.1, 22.7, 14.1. M (EI) m/z: 289, 246, 218, 204, 162, 149, 136, 109, 93, 55. H 2 H 2 Bis(2-aminophenyl)disulfide (4) 14 1 H MR (400 MHz, CDCl 3 ) δ 7.18 (t, J = 7.0 Hz, 4H), 6.73 (d, J = 8.3 Hz, 2H), 6.62 (t, J = 7.5 Hz, 2H), 4.27 (s, 4H). 13 C MR (100 MHz, CDCl 3 ) δ 148.5, 136.7, 131.5, 118.7, 118.2, 115.2. M (EI) m/z: 248, 231, 214, 184, 155, 124, 98, 93, 80. Bis(4-methylphenyl)disulfide (5) 15 1 H MR (400 MHz, CDCl 3 ) δ 7.36 (d, J = 8.0 Hz, 4H), 7.07 (d, J = 8.0 Hz, 4H), 2.28 (s, 6H). 13 C MR (100 MHz, CDCl 3 ) δ 137.3, 133.8, 129.7, 128.4, 21.0. M (EI) m/z: 246, 213, 198, 182, 167, 154, 123, 91, 79, 65. D. References (1) Deng, H.; Li, Z.; Ke, F.; Zhou, X. Chem. Eur. J. 2012, 18, 4840. (2) Ranjit,.; Liu, X. Chem. Eur. J. 2011, 17, 1105. (3) Melzig, L.; Metzger, A.; Knochel, P. Chem. Eur. J. 2011, 17, 2948. (4) Huang, J.; Chan, J.; Chen, Y.; Borths, C. J.; Baucom, K. D.; Larsen, R. D.; Faul, M. M. J. Am. Chem. oc. 2010, 132, 3674. (5) Fan, X.; Wang, Y.; He, Y.; Zhang, X.; Wang, J. Tetrahedron Lett. 2010, 51, 3493. (6) Wang, H.; Wang, L.; hang, J.; Li, X.; Wang, H.; Gui, J.; Lei, A. Chem. Commun. 2012, 48, 76. (7) Yamamoto, T.; Muto, K.; Komiyama, M.; Canivet, J.; Yamaguchi, J.; Itami, K. Chem. Eur. J. 2011, 17, 10113. (8) Tomilov, Y. V.; Platonov, D..; Frumkin, A. E.; Lipilin, D. L.; alikov, R. F. Tetrahedron Lett. 2010, 51, 5120. (9) Fan, X.; He, Y.; Zhang, X.; Guo,.; Wang, Y. Tetrahedron 2011, 67, 6369. (10) Chakraborti, A. K.; elvam, C.; Kaur, G.; Bhagat,. ynlett 2004, 15, 851. (11) Abbotto, A.; Bradamante,.; Facchetti, A.; Pagani, G. A. J. Org. Chem. 2002, 67, 5753. (12) Yao, T.; Hirano, K.; atoh, T.; Miura, M. Chem. Eur. J. 2010, 16, 12307. (13) eijas, J. A.; Vazquez-Tato, M. P.; Carballido-Reboredo, M. R.; Crecente-Campo, J.; Romar-Lopez, L. ynlett 2007, 18, 313. 7

(14) Garcia Ruano, J. L.; Parra, A.; Aleman, J. Green Chem. 2008, 10, 706. (15) Loghmani-Khouzani, H.; Poorheravi, M. R.; adeghi, M. M. M.; Caggiano, L.; Jackson, R. F. W. Tetrahedron 2008, 64, 7419. 8

E. MR pectra 1 H MR and 13 C MR of 2-Phenylbenzo[d]thiazole (3a) 9

1 H MR and 13 C MR of 2-p-Tolylbenzo[d]thiazole (3b) 10

1 H MR and 13 C MR of 2-(4-Methoxyphenyl)benzo[d]thiazole (3c) 11

1 H MR and 13 C MR of 2-(4-isopropylphenyl)benzo[d]thiazole (3d) 12

1 H MR and 13 C MR of 4-(Benzo[d]thiazol-2-yl)-,-dimethylbenzenamine (3e) 13

1 H MR and 13 C MR of 2-(4-(Trifluoromethyl)phenyl)benzo[d]thiazole (3f) 14

1 H MR and 13 C MR of 4-(Benzo[d]thiazol-2-yl)benzonitrile (3g) 15

1 H MR and 13 C MR of 2-(4-Fuorophenyl)benzo[d]thiazole (3h) 16

1 H MR and 13 C MR of 2-(4-Chlorophenyl)benzo[d]thiazole (3i) 17

1 H MR and 13 C MR of 2-(4-Bromophenyl)benzo[d]thiazole (3j) 18

1 H MR and 13 C MR of 2-(4-Iodophenyl)benzo[d]thiazole (3k) 19

1 H MR and 13 C MR of 2-(3-Bromo-4-methylphenyl)benzo[d]thiazole (3l) 20

1 H MR and 13 C MR of 2-(aphthalen-3-yl)benzo[d]thiazole (3m) 21

1 H MR and 13 C MR of 2-(Furan-2-yl)benzo[d]thiazole (3n) 22

1 H MR and 13 C MR of 5-Chloro-2-phenylbenzo[d]thiazole (3o) 23

1 H MR and 13 C MR of 2-Methylbenzo[d]thiazole (3p) 24

1 H MR and 13 C MR of 2-Cyclopropylbenzo[d]thiazole (3q) 25

1 H MR and 13 C MR of 2-Benzylbenzo[d]thiazole (3r) 26

1 H MR and 13 C MR of 2-(3-Methoxybenzyl)benzo[d]thiazole (3s) 27

1 H MR and 13 C MR of 2-((Pyridin-2-yl)methyl)benzo[d]thiazole (3t) 28

1 H MR and 13 C MR of 2-((Thiophen-3-yl)methyl)benzo[d]thiazole (3u) 29

1 H MR and 13 C MR of 2-(2-Methoxyethyl)benzo[d]thiazole (3v) 30

1 H MR and 13 C MR of 2-(3-Phenylpropyl)benzo[d]thiazole (3w) 31

1 H MR and 13 C MR of 2-Undecylbenzo[d]thiazole (3x) 32

1 H MR and 13 C MR of Bis(2-aminophenyl)disulfide (4) 33

1 H MR and 13 C MR of Bis(4-methylphenyl)disulfide (5) 34