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 |
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1a: 0.1 mmol, 2a: 0.25 mmol, blue light (λmax 448/455 nm).
Determined by 1H NMR analysis of the crude reaction mixture with 1,1,2,2-tetrachloroethane as an internal standard.
Determined by chiral stationary phase HPLC analysis.
Isolated yield.
Without a photocatalyst.
Reaction in the dark.
Without a Cu(i) catalyst.