Table 1 Screening of the reaction conditions.a

From: Metal-free electrochemical dihydroxylation of unactivated alkenes

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Entry

Variation from standard conditions

Yield (%)b

1

None

80

2

Me4NI instead of Et4NI

75

3

nPr4NI instead of Et4NI

72

4

nBu4NI instead of Et4NI

66

5

nBu4NBF4 instead of Et4NI

0

6

w/o NH4I

62

7

w/o TFA

45

8

w/o Et4NI

trace

9

iPrOH instead of tBuOH

49

10

MeOH instead of tBuOH

0

11

TFE instead of tBuOH

0

12

CF (+) | Ni (-)

78

13

CF (+) | CF (-)

trace

  1. Bold formatting shows that entry 1 is the optimal reaction condition.
  2. aReaction conditions. 1a (0.3 mmol), Et4NI (2.0 equiv.), NH4I (2.0 equiv.), TFA (3.0 equiv.), tBuOH (3.0 mL) and H2O (1.0 mL) under 50 mA constant in an undivided cell at 50 oC for 12 h with carbon felt (CF) as anode and Pt plate as cathode.
  3. bIsolated yield. TFA = trifluoroacetic acid; TFE = 2,2,2-trifluoroethanol.