Table 1 Optimization of the reaction conditions^a


Entry	Variations from “conditions”	Yield^b
1	None	82%
2	4CzIPN instead of Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆	54%
3	Ni(bpy)Br₂ instead of Ni(dtbbpy)Br₂	33%
4	MeCN instead of MeCN:DMA (9:1)	68%
5	DMA instead of MeCN:DMA (9:1)	45%
6	DMSO instead of MeCN:DMA (9:1)	31%
7	No TBAB	65%
8	40 °C instead of 60 °C	70%
9	2.0 equiv. of 2	90%
10^c	No light	0
11^d	No nickel catalyst	0
12^e	No photocatalyst	0

TBAB tetrabutylammonium bromide, 4CzIPN 2,4,5,6-tetra(9H-carbazol-9-yl)−1,3-benzenedicarbonitrile, DMA N,N-dimethylacetamide.
^aReactions were performed with 1 (0.2 mmol), 2 (0.3 mmol), photocatalyst (0.004 mmol), nickel catalyst (0.04 mmol), base (0.33 mmol), and additive (0.05 mmol) in 2.0 mL MeCN/DMA (9/1, V/V), were placed at approximately 8 cm away from two parallel LEDs (Blue LEDs, 455 nm, 18 W), and were heated at 60 °C in an oil bath for 48 h.
^bYield of isolated product.
^cWithout light.
^dWithout nickel catalyst.
^eWithout photocatalyst.

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