Table 1 Optimization conditions for forming 3a

From: Azoarene activation for Schmidt-type reaction and mechanistic insights

Entry

[Au] (1 mol%)

Solvent

Yield (%)b

1

JohnPhosAu(MeCN)SbF6

DCE

65

2

Ph3PAuCl

DCE

56

3

XPhosAuCl

DCE

48

4

SPhosAuCl

DCE

trace

5

IPrAuNTf2

DCE

29

6

AuCl3

DCE

25

7

AuCl

DCE

15

8

JohnPhosAu(MeCN)SbF6

THF

N.R.

9

JohnPhosAu(MeCN)SbF6

Acetone

N.R.

10

JohnPhosAu(MeCN)SbF6

DCM

50

11

JohnPhosAu(MeCN)SbF6

Toluene

25

12c

JohnPhosAu(MeCN)SbF6

DCE

54

13d

JohnPhosAu(MeCN)SbF6

DCE

49

  1. aReaction conditions: 1a (0.2 mmol), 2a (0.4 mmol), and at room temperature in the solvent (2.0 ml) for 6 h.
  2. bIsolated yield based on 1a.
  3. cThe reaction was conducted at 40 °C for 6 h.
  4. dThe reaction was conducted at 55 °C for 6 h.
  5. N.R. = not reaction. JohnPhos = 2-(di-tert-butylphosphino)biphenyl, SPhos = 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl, XPhos = 2-(dicyclohexylphosphino)-2’,4’,6’-tri-i-propyl-1,1’-biphenyl, IPr =  isopropyl, NTf2 = bis(trifluoromethylsulfonyl)imide.
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