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. 2020 Sep 28;11(42):11492–11497. doi: 10.1039/d0sc03776a

Optimization of the reaction conditionsa.

graphic file with name d0sc03776a-u1.jpg
Entry Metal salt Ligand Yieldb (%) drc eed (%)
1 Sc(OTf)3 L3-PiMe3 48 >19 : 1 25
2 Mg(OTf)2 L3-PiMe3 80 >19 : 1 77
3 Ni(OTf)2 L3-PiMe3 85 >19 : 1 80
4 Ni(NTf2)2 L3-PiMe3 87 >19 : 1 80
5 Ni(BF4)2·6H2O L3-PiMe3 86 >19 : 1 83
6 Ni(BF4)2·6H2O L3-PrMe3 80 >19 : 1 82
7 Ni(BF4)2·6H2O L3-RaMe3 76 >19 : 1 70
8 Ni(BF4)2·6H2O L3-PiMe2 84 >19 : 1 86
9 Ni(BF4)2·6H2O L3-PiEt2 88 >19 : 1 91
10 Ni(BF4)2·6H2O L3-PiPr2 95 >19 : 1 71
11e Ni(BF4)2·6H2O L3-PiEt2 95 >19 : 1 92
12e,f Ni(BF4)2·6H2O L3-PiEt2 86 >19 : 1 92
a

Unless otherwise noted, all the reactions were carried out with 1a (0.10 mmol), 2a (0.10 mmol) and metal salt/ligand (1 : 1, 10 mol%) in CH2Cl2 (1.0 mL) at 30 °C for 24 h.

b

Isolated yield of 3aa.

c

Determined by 1H NMR.

d

Determined by HPLC analysis on a chiral stationary phase.

e

2a (2.0 equiv.) was used.

f

5 mol% catalyst loading.