Table 1 Optimization of reaction conditionsa.

From: Site-selective electrooxidation of methylarenes to aromatic acetals

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Entry

Deviation from standard conditions

Yield (%)b

1

None

72c

2

Reaction at RT

25

3

Reaction at 8 mA

61

4

Reaction at 12 mA

66

5

Reaction under air

50

6

Et4NPF6 (0.2 equiv)

63

7

Et4NBF4 instead of Et4NPF6

72

8

n-Bu4NPF6 instead of Et4NPF6

64

9

Et4NOTs instead of Et4NPF6

66

10

Pt plate (1 cm × 1 cm) as anode

20 (69)d

11

Graphite plate (1 cm × 1 cm) as anode

56

  1. Bn benzyl
  2. aReaction conditions: RVC anode, Pt plate cathode, 1 (0.2 mmol), MeOH (9 mL), Et4NPF6 (0.1 mmol), 10 mA, 2.3 h (4.3 F mol–1).
  3. bDetermined by 1H NMR analysis using 1,3,5-trimethoxybenzene as the internal standard.
  4. cIsolated yield.
  5. dUnreacted 1 in bracket.