Table 1. Nickel-catalyzed arylfluoroalkylation: optimization of conditions ^a .

Entry	Ni source	Ligand	Base	E/Z b	Yield c (%)
1 d	NiCl2(PPh3)2	XantPhos	LDA	4 : 1	85
2 e	NiCl2(PPh3)2	XantPhos	LDA	7 : 1	72
3	NiCl2(PPh3)2	XantPhos	LDA	>99 : 1	91
4	NiCl2(PPh3)2	XantPhos	tBuOK	—	Trace
5	NiCl2(PPh3)2	XantPhos	LiHMDS	>99 : 1	59
6	NiCl2(PPh3)2	XantPhos	KHMDS	>99 : 1	44
7	NiCl2	XantPhos	LDA	>99 : 1	45
8	Ni(OTf)2	XantPhos	LDA	>99 : 1	14
9	NiCl2·glyme	XantPhos	LDA	>99 : 1	61
10	Ni(COD)2	XantPhos	LDA	>99 : 1	85
11	NiCl2(PPh3)2	PPh3	LDA	>99 : 1	38
12	NiCl2(PPh3)2	P(1-Naph)3	LDA	>99 : 1	32
13	NiCl2(PPh3)2	dppBz	LDA	>99 : 1	32
14	NiCl2(PPh3)2	Phen	LDA	>99 : 1	36
15	NiCl2(PPh3)2	dmbPy	LDA	>99 : 1	20
16	NiCl2(PPh3)2	IPr·HCl	LDA	>99 : 1	18
17 f	NiCl2(PPh3)2	XantPhos	LDA	>99 : 1	91
18 g	NiCl2(PPh3)2	XantPhos	LDA	>99 : 1	62
19	—	XantPhos	LDA	—	Trace

^aUnless otherwise noted, the reaction conditions were as follows: 1a (0.2 mmol), 2 (3.0 equiv.), [Ni] (10 mol%), ligand (10 mol%), base (105 mol%), solvent (2.0 mL), –10 °C, 12 h, N₂.

^b E/Z ratio was determined by ¹⁹F NMR analysis.

^cYields of the isolated products given.

^dBrCF₂CO₂Et was used as 2a.

^eBrCF₂CONEt₂ was used as 2b.

^f T = –30 °C.

^g T = 0 °C. XantPhos = 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, dmbPy = 4,4′-dimethyl-2,2′-bipyridine, dppBz = 1,2-bis(diphenylphosphino)benzene, Phen = 1,10-phenanthroline.