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. Author manuscript; available in PMC: 2019 Jun 20.
Published in final edited form as: J Am Chem Soc. 2018 Jun 11;140(24):7667–7673. doi: 10.1021/jacs.8b03744

Table 1.

Reaction Development and Control Experimentsa

graphic file with name nihms977308u2.jpg

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
a

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.

b

Yield determined by 19F NMR.

c

Isolated yield.

d

Deoxygenated reaction mixture sparged with air for 2 min prior to light irradiation.