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. Author manuscript; available in PMC: 2020 Dec 26.
Published in final edited form as: J Am Chem Soc. 2019 Dec 13;141(51):20069–20078. doi: 10.1021/jacs.9b08282

Table 1.

Selected Optimization for Ni/Photoredox DCFa

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entry deviation from standard conditions NMR yield of 4
1 none 70% (69%)c
2 no base 55%
3 0.05 M concentration 67%
4 0.25 M concentration 39%
5 Kessil lamp in place of blue LEDs 60%
6 5 mol % [Ir] cat, 3 mol % [Ni] 59%
7 5 mol % [Ir] cat, 10 mol % [Ni] 66%
8 CI-4CzIPN in place of [Ir] (40%)c
9 “zero precautions” 44%d
10 No [Ni] catalyst 0%
11 No [Ir] photocatalyst 0%
12 No light 0%
a

Optimization performed using 4-chloro-1-bromobenzene (0.1 mmol) for 16 h at 27 °C; [Ir] = [Ir{dF(CF3)2ppy}2(bpy)]PF6.

b

Yields in parentheses are isolated yield of 4 after purification.

c

Reaction performed using 2,4,5,6-tetrakis(3,6-dichloro-9H-carbazol-9-yl)isophthalonitrile (Cl-4CzIPN) as the photocatalyst.

d

Reaction performed under air with non-rigorously dried solvent.