Table 1.
| ||
---|---|---|
entry | deviation from conditions above | yieldb (%) |
1 | no light (rt or 80 °C) | 0 |
2 | 13 W 405 nm LED | 93 |
3 | no nickel salt | 0 |
4 | 5 mol% NiBr2·glyme | 95 |
5 | 5 mol% NiCl2·6H2O | 95 |
6 | no quinuclidine base | 55 |
7 | no quinuclidine, 3.5 equiv morpholine | 94 (87)c |
8 | 1.5 equiv DBU base | 2 |
9 | same as entry 7, presence of oxygend | 91 |
10 | 1 h | 72 |
0.4 mmol scale. Abbreviations: DMAc, N,N-dimethylacetamide; rt, room temperature; LED, light-emitting diode; DBU, 1,8-diazabicyclo-[5.4.0]undec-7-ene.
Yield determined by 19F NMR.
Isolated yield.
Deoxygenated reaction mixture sparged with air for 2 min prior to light irradiation.