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Table 2 CuO@ARF-catalyzed C-S cross-coupling reactions between haloarenes and thiol a

From: An efficient heterogeneous catalyst (CuO@ARF) for on-water C-S coupling reaction: an application to the synthesis of phenothiazine structural scaffold

Entry Aryl halide Thiol Time (h) Product Yield (%)b
1 (4-H3CO)C6H4I C6H5SH 8 (4-H3CO)H4C6 - S - C6H5 90
2 (3-H3CO)C6H4I (4-C1)C6H4SH 12 (3-H3CO)H4C6 - S - C6H4(4-C1) 85
3 (2-H3CO)C6H4I (4-CH3)C6H4SH 18 (2-H3CO)H4C6 - S - C6H4(4-CH3) 75
4 (3-NO2)C6H4I (4-CH3)C6H4SH 11 (3-NO2)H4C6 - S - C6H4(4-CH3) 78
5 (4-H3CO)C6H4I (4-CH3)C6H4SH 10 (4-H3CO)H4C6 - S - C6H4(4′-CH3) 75
6 (4-H3C)C6H4Br C6H5SH 24 No reaction -
7 (4-CH3CO)C6H4C1 C6H5SH 24 No reaction -
8c (4-H3C)C6H4Br C6H5SH 24 No reaction -
9 (5-Br)(2-H3CO)C6H3I C6H5SH 8 (5-Br)(2-H3CO)H3C6 - S - C6H5 90
10 (3-Br)C6H4I (4-CH3)C6H4SH 16 (3-Br)H4C6 - S - C6H4(4-CH3) 79
11 (3-C1)C6H4I (4-CH3)C6H4SH 16 (3-C1)H4C6 - S - C6H4(4-CH3) 79
12 (4-H3CO)C6H4I (2,5-(CH3)2)C6H4SH 7 (4-H3CO)H4C6 - S - C6H3(2,5-(CH3)2) 89
13 (4-H3CO)C6H4I CySH 16 (4-H3CO)H4C6 - S - Cy 70
14 (4-H3CO)C6H4I n-C5H11SH 16 (4-H3CO)H4C6 - S - C5H11-n 73
15 (3-H3CO)C6H4I n-C7H11SH 16 (4-H3CO)H4C6 - S - C7H15-n 76
16d 1,3-C6H4I2 (4-CH3)C6H4SH 14 1,3-((4-CH3)C6H4S)2 - C6H4 79
17 (2-Br)C6H4I (2-NH2)C6H4SH 8 (2-Br)H4C6 - S - C6H4(2-NH2) 82
  1. aAryl halide: thiol: catalyst (1 mmol: 1.2 mmol: 200 mg), SDS (10 mol%), and K2CO3 (1.1 mmol) were taken in water (3 mL) and heated at 100°C. bYield refers to pure isolated products characterized by spectroscopic (1H and 13C NMR) data. cCatalyst (300 mg mmol−1 of aryl bromide), SDS (10 mol%), and Cs2CO3 (1.1 mmol). dAryl halide: thiol: catalyst (0.5 mmol: 1.2 mmol: 200 mg), SDS (10 mol%), and K2CO3 (1.1 mmol) were taken in water (3 mL).