Table 1 Optimization of reaction conditions for intramolecular allylic C–H amination.

From: Tailored cobalt-salen complexes enable electrocatalytic intramolecular allylic C–H functionalizations

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Entry

Deviation from standard conditions

Yield of 2 (%)a

1

None

86b

2

No [Co]-1

0

3

Reaction at rt

Trace

4

No Na2CO3

52 (46)c

5

5 mol% of [Co]-1

87d

6

Et4NPF6 (0.1 equiv.)

85

7

[Co]-2, or [Co]-3, or [Co]-4 as catalyst

50–63

8

Brass (1 cm × 1 cm) as cathode

82

9

Nickel plate (1 cm × 1 cm) as cathode

83

10

Graphite plate (1 cm × 1 cm) as cathode

29 (58)c

11

Under air

86

  1. Reaction conditions: RVC (1 cm × 1 cm × 1.2 cm), Pt plate cathode (1 cm × 1 cm), 1 (0.2 mmol), MeCN (5 mL), MeOH (1 mL), constant current = 10 mA, 4 h (7.5 F mol–1). Compound 2 was formed as a single diastereomer under all conditions.
  2. PMP p-methoxypenyl.
  3. aDetermined by 1H NMR analysis using 1,3,5-trimethoxybenzene as the internal standard.
  4. bIsolated yield.
  5. cUnreacted 1 in brackets.
  6. d2′ was formed in a 4% yield.
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