Table 1.

Further reaction optimization^a

entry	deviation in reaction condition	yields of 3 (%)b
1	none	75 (72)c
2	Lithium-1-adamantanolate (LiOAd) instead of LiOtBu	75
3	LiOMe instead of LiOtBu	23
4	LiOiPr instead of LiOtBu	15
5	1 equiv LiOtBu instead of 1.5 equiv	42
6	2 equiv LiOtBu instead of 1.5 equiv	65
7	NiI2 or NiCl2·DME instead of NiBr2.DME	70–72
8	Ni(TMHD)2 instead of NiBr2·DME	53
9	Ni(PPh3)4 instead of NiBr2·DME	12
10	Ni(cod)2 instead of NiBr2·DME	52
11	other metals instead of NiBr2·DMEd	0
12	room temperature instead of 80 °C	10
13	60 °C instead of 80 °C	62
14	2-Me-THF instead of THF	70
15	1,4-dioxane instead of THF	60
16	MeCN or toluene instead of THF	35–38
17	NMP, DMF, DMSO or dioxane instead of THF	0–25

^aReactions run at 0.10 mmol scale in 0.5 mL solvent.

^b1H NMR yields with pyrene as a standard.

^cThe yield of isolated product from a 0.50 mmol scale reaction in 2.5 mL THF in parenthesis. dr is 1.1:1.

^dPd(OAc)₂, CuI, Co(OAc)₂, FeCl₂.