Table 2 Metal-catalyzed S-amidation of primary thiol 4 with 2

From: Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols

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Entry

Conditions

Yield (%)a

5ab/5b/5c

1

4 (2 equiv), 2 (1 equiv), IPrCuCl (5 mol%)

31/ND/69

2

4 (1 equiv), 2 (2 equiv), IPrCuCl (5 mol%)

57/ND/42

3

4 (1 equiv), 2 (2 equiv), IPrCuCl (5 mol%), AgSbF6 (5 mol%)

61/ND/39

4

4 (1 equiv), 2 (2 equiv), IPrCuCl (5 mol%), AgBF4 (5 mol%)

65/ND/35

5

4 (1 equiv), 2 (2 equiv), IPrCuCl (5 mol%), NaBArF4 (5 mol%)

48/ND/52

6

4 (1 equiv), 2 (2 equiv), IPrCuCl (5 mol%), Ag2CO3 (5 mol%)

69/ND/28

7

4 (1 equiv), 2 (2 equiv), IPrCuCl (5 mol%), Ag2CO3 (10 mol%)

74(72c)b/ND/22

8

4 (1 equiv), 2 (2 equiv), IPrCuCl (5 mol%), Ag2CO3 (20 mol%)

53/ND/17

9

4 (1 equiv), 2 (2 equiv), Ag2CO3 (10 mol%)

ND/ND/ND

10

4 (1 equiv), 2 (2 equiv), IPrAgCl (5 mol%)

ND/ND/ND

  1. ND not detected.
  2. aAll screening reactions were carried at a 0.2 mmol scale; yields are based on 1H NMR analysis of crude reaction mixture.
  3. b>99.9% ee for 5a.
  4. cIsolated yields at a 15.0 mmol scale.
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