Table 1 Optimization of the reaction conditions.

From: Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process

View full size image

Entry

Ligand

Solvent

Yield of 2aa

Recovery of 1aa

1

–

DMF

29

18

2

L1

DMF

7

88

3

L2

DMF

28

65

4

L3

DMF

52

38

5

L4

DMF

53

32

6

L5

DMF

61

33

7

L5

CH3CN

80

14

8b

L5

CH3CN

87

11

9c

L5

CH3CN

94(89d)

Trace

10e

L5

CH3CN

0

99

11c,f

L5

CH3CN

0

100

12c,g

L5

CH3CN

0

99

13c,h

L5

CH3CN

0

100

  1. aDetermined by 1H NMR analysis with CH2Br2 as the internal standard.
  2. b3 equivalents of TMSCN were used.
  3. cThe reaction was conducted on 0.5 mmol scale using TMSCN (3 equiv) in CH3CN (5 mL).
  4. dIsolated yield.
  5. eCuBr2 was used instead of CuBr.
  6. fWithout light.
  7. gThe reaction was conducted in 50 °C oil bath without light.
  8. hWithout fac-Ir(ppy)3.