Table 1 Optimization of reaction conditions

From: A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols

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Entry

Photocatalyst

Ligand

Solvent

Yield of 3ca (%)

ee of 3ca (%)

1b

PC (20 mol%)

L1

EtOAc

30

60

2

PC (20 mol%)

L2

EtOAc

24

45

3

PC (20 mol%)

L3

EtOAc

10

36

4

PC (20 mol%)

L4

EtOAc

42

30

5

PC (20 mol%)

L5

EtOAc

11

35

6

PC (20 mol%)

L6

EtOAc

43

80

7

TBADT (2 mol%)

L6

Acetone

47

85

8

TBADT (2 mol%)

L6

Acetone:PhCF3 = 1:1

47

90

9c

TBADT (5 mol%)

L6

Acetone:PhCF3 = 1:1

71

90

  1. All reactions were carried out on a 0.2 mmol scale with respect to aryl bromide (2a). Conditions: NiBr2.DME (10 mol%), chiral ligand L (15 mol%), 2a (0.2 mmol), 1 (1.0 mmol), K3PO4 (0.24 mmol), photocatalyst, solvent (2.0 mL, 0.1 M) under the irradiation of LEDs (10 W, 390 nm) at 25 °C for 60 h. Yields are for isolated and purified products. The ee values were determined by HPLC using a chiral stationary phase.
  2. NP no product.
  3. aThe reaction was performed in EtOAc at 25 °C using PC as photocatalyst and L1 as ligand.
  4. bThe reaction was performed at −5 °C.
  5. cAcetone/PhCF3 (1.0 mL, 0.2 M).