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. 2020 Apr 27;11(20):5168–5174. doi: 10.1039/d0sc01890b

Screening of the reaction conditionsa.

Entry Ligand Solvent Temp (°C) Yieldb (%) eec (%)
1 L1 MeCN 23 10 ND
2 L2 MeCN 23 72 30
3 L2 MeCN 5 61 70
4 L2 MeCN −20 62 89
5 L3 MeCN 5 49 52
6 L4 MeCN 5 43 −44
7 L2 EtOH 5 73 74
8 L2 EtOH −20 Trace ND
9 L2 EtOH : MeCN (1 : 1) −20 68 66
10 L2 EtOH : DME (1 : 1) −20 77 76
11 L2 EtOH : DME (3 : 1) −20 49 85
12 L2 EtOH:DME (1:3) −20 83(80) d 89
13 L2 EtOH : DME (1 : 3) −30 67 89
14e L2 EtOH : DME (1 : 3) −20 Trace ND
15f L2 EtOH : DME (1 : 3) −20 Trace ND
16g L2 EtOH : DME (1 : 3) −20 Trace ND
graphic file with name d0sc01890b-u2.jpg
a

1a: 0.1 mmol, 2a: 0.25 mmol, blue light (λmax 448/455 nm).

b

Determined by 1H NMR analysis of the crude reaction mixture with 1,1,2,2-tetrachloroethane as an internal standard.

c

Determined by chiral stationary phase HPLC analysis.

d

Isolated yield.

e

Without a photocatalyst.

f

Reaction in the dark.

g

Without a Cu(i) catalyst.