Table 1 Metal-catalyzed S-amidation of secondary thiol 1 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

3a/3b/3c

1

1 (2 equiv), 2 (1 equiv), [Cp*RuCl2]2 (2.5 mol%), DCE

16/39/15

2

1 (2 equiv), 2 (1 equiv), FeCl2·4H2O (5 mol%), DCE

21/51/9

3

1 (2 equiv), 2 (1 equiv), FeCl2·PDI (5 mol%), DCE

17/32/5

4

1 (2 equiv), 2 (1 equiv), Cu(OAc)2 (5 mol%), DCE

27/ND/4

5

1 (2 equiv), 2 (1 equiv), CuOAc (5 mol%), DCE

53/ND/8

6

1 (2 equiv), 2 (1 equiv), CuOAc (5 mol%), n-hexane

83/ND/11

7

1 (2 equiv), 2 (1 equiv), CuOAc (5 mol%), CH3CN

29/ND/9

8

1 (2 equiv), 2 (1 equiv), CuOAc (5 mol%), HFIP

11/ND/4

9

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

95 (91b)/ND/5

10

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

67/ND/1

11

1 (2 equiv), 2 (1 equiv), IPrCuCl (5 mol%), n-hexane

37/ND/9

12

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

57/11/19

13

1 (2 equiv), 2 (1 equiv), IPrCuCl (5 mol%), HFIP/H2O (10/1)

86/ND/3

14

1 (2 equiv), 2 (1 equiv), SIPrCuCl (5 mol%), HFIP

86/ND/3

15

1 (2 equiv), 2 (1 equiv), IMesCuCl (5 mol%), HFIP

32/ND/ND

16

1 (2 equiv), 2 (1 equiv), IPrCuBr (5 mol%), HFIP

93/ND/2

17

1 (2 equiv), 2 (1 equiv), IPrCuI (5 mol%), HFIP

68/ND/2

18

1 (2 equiv), 2 (1 equiv), IAdCuCl (5 mol%), HFIP

85/ND/2

19

1 (2 equiv), 2 (1 equiv), IPrCuCl (5 mol%), HFIP, 10 °C

8/ND/ND

20

1 (2 equiv), 2 (1 equiv), IPrCuCl (5 mol%), HFIP (0.05 M)

67/ND/3

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  1. ND not detected, dipp 2,6-diisopropylphenyl, Mes mesityl, Ad admantyl.
  2. aAll screening reactions were carried at a 0.2 mmol scale; yields were based on 1H NMR analysis of crude reaction mixture after workup.
  3. bIsolated yield at a 0.4 mmol scale.
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