Table 1 Ligand effect on the enantioselective formal reductive alkyl-alkyl cross-coupling reactiona

From: Ligand-enabled Ni-catalysed enantioconvergent intermolecular Alkyl-Alkyl cross-coupling between distinct Alkyl halides

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Entry

L

Yield (%)

ee (%)

Entry

L

Yield (%)

ee (%)

Entry

L

Yield (%)

ee (%)

1

L1

67

70

9

L9

24

72

17

L17

8

50

2

L2

15

36

10

L10

49

84

18

L18

44

86

3

L3

16

38

11

L11

30

83

19

L19

45

91

4

L4

27

42

12

L12

22

62

20

L20

21

94

5

L5

39

76

13

L13

31

60

21

L21

18

91

6

L6

30

71

14

L14

26

68

22

L22

10

78

7

L7

trace

15

L15

18

62

23

L23

23

87

8

L8

29

60

16

L16

29

90

24b

L20

85 (76)c

94

  1. DME dimethoxyethane, DMA dimethylacetamide.
  2. aThe reaction was conducted using 1a (0.2 mmol), 2a (0.6 mmol) under indicated conditions for 24 h. Yield was determined by GC using n-dodecane as internal standard. The enantiomeric excess was determined by HPLC using a chiral column with stationary chiral phase.
  3. bReaction conditions: The reaction was run using 1a (0.2 mmol), 2a (0.6 mmol) with NiCl2‧DME (8 mol%), L20 (8 mol%), FeCl2 (25 mol%), Zn (2.0 equiv), CsI (3.0 equiv), 15-crown-5 (10 mol%) in DMA/diglyme = 1:3 (0.1 M) at room temperature for 24 h.
  4. cIsolated yield after flash chromatography.