Table 2 Optimization of reaction conditionsa, b

From: Accessing gold p-acid reactivity under electrochemical anode oxidation (EAO) through oxidation relay

View full size image

Entry

Variation from “standard conditions”

convn. (2a)

3ac

4adc

1

none

100%

32%

29%

2

MeCN:MeOH = 4:1

100%

16%

30%

3

MeCN:MeOH = 1:1

100%

12%

26%

4

tBuOH instead of MeOH

100%

10%

22%

5

DCM instead of MeOH

100%

0%

48%

6

Other [Au]

100%

<15%

Up to 50%

7

Other electrolytes

100%

Up to 35%

Up to 40%

8

Double concentration (1a, 2a, [Au])

100%

54%

22%

9

3 eq. 2a

100%

40%

27%

10

0.5 mmol 1a, 1.5 mmol 2a, 0.05 mmol [Au]

100%

70%

21%

11

0.5 mmol 1a, 1.5 mmol 2a, 0.05 mmol [Au]

(Add 0.5 mmol 2a, run rxn for 10 h)*3

100%

(100% for 1a)

92%

18%

12

No [Au]

100%

0%

57%

13

No current

0%

  1. aConditions: 1a (0.2 mmol), 2a (0.4 mmol), Ph3PAuCl (0.02 mmol), nBu4NPF6 (1 mmol), MeCN (5 mL), MeOH (0.5 mL), C/Pt, 5 mA constant current, undivided cell, air, rt, 12 h.
  2. b1H NMR yields using 1,3,5-trimethoxybenzene as an internal standard.
  3. c3a yield based on 1a, 4ad yield based on 2a.