Table 1 Optimization of the reaction conditions View full size image

From: Ni(II)-catalyzed asymmetric alkenylation and arylation of aryl ketones with organoborons via 1,5-metalate shift

Entry

Metal salt

Ligand

Yield (%)a

ee (%)b

1

Ni(OAc)2

L1

<5

–

2

Ni(OAc)2

L2

<5

–

3

Ni(OAc)2

L3

<5

–

4

Ni(OAc)2

L4

30

<5

5

Ni(OAc)2

L5

9

86

6

Ni(OAc)2

L6

55

92

7

Ni(OAc)2

L7

60

93

8

Ni(OAc)2

L8

66

94

9

Ni(OAc)2

L9

56

90

10

Ni(ClO4)2‧6H2O

L8

69

94

11

FeCl3

L8

NP

–

12

CoBr2

L8

NP

–

13

Cu(OAc)2

L8

NP

–

14

Zn(OTf)2

L8

NP

–

15c

Ni(ClO4)2‧6H2O

L8

84

94

16d

Ni(ClO4)2‧6H2O

L8

95

94

17d,e

Ni(ClO4)2‧6H2O

L8

96

94

18d–f

Ni(ClO4)2‧6H2O

L8

96 (92)

94

19d–g

Ni(ClO4)2‧6H2O

L8

76

94

20e–h

Ni(ClO4)2‧6H2O

L8

83

94

  1. Reactions were carried out with 1a (0.10 mmol), 2a (0.15 mmol), Na3PO4 (0.20 mmol), metal salt (10 mol%), and ligand (12 mol%) in TFE (2 mL) at 70 °C for 24 h.
  2. NP no product.
  3. aDetermined by 1H NMR analysis; isolated yield shown in parenthesis.
  4. bDetermined by chiral HPLC analysis.
  5. cTFE (1 mL).
  6. dTFE (0.5 mL).
  7. eWith preprepared NiL8(ClO4).
  8. f1 h.
  9. gNiL8(ClO4)2 (5 mol%).
  10. hTFE (0.25 mL).
Back to article page