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. 2019 Aug 20;4(10):14353–14359. doi: 10.1021/acsomega.9b02442

Table 1. Optimization of the Reaction Conditionsa.

graphic file with name ao9b02442_0008.jpg

entry electrode electrolyte current (mA) additive time (h) yield (%)b
1 C/C LiClO4 10   3 60
2c C/C LiClO4 10   3 52
3 C/C LiClO4 10 AcOH 3 43
4 C/C LiClO4 10 TsOH 3 77
5 C/C LiClO4 10 TsOH 4.5 72
6 C/C LiClO4 10 TsOH 2.5 79
7 C/C LiClO4 10 TsOH 2 74
8 C/C LiClO4 5 TsOH 4.5 78
9 C/C LiClO4 15 TsOH 2 74
10 C/Pt LiClO4 10 TsOH 2.5 66
11 C/Ni LiClO4 10 TsOH 2.5 51
12 C/Cu LiClO4 10 TsOH 2.5 32
13 C/Fe LiClO4 10 TsOH 2.5 31
14 C/C Bu4NBF4 10 TsOH 2.5 63
15 C/C   10 TsOH 2.5 82
16 C/C   10   2.5 53
17d C/C   10 TsOH 2.5 67
18e C/C   10 TsOH 2.5 68
19f C/C   10 TsOH 2.5 0
a

Reaction conditions: 1a (0.5 mmol), 2a (2.0 equiv), MeOH (8 mL), electrolyte (0.5 mmol), additive (0.5 mmol), 4 Å MS (200 mg), undivided cell, room temperature, and nitrogen atmosphere.

b

Yields based on 1a.

c

Under air without 4 Å MS.

d

2a (1.5 equiv).

e

2a (3.0 equiv).

f

Without electric current.