Table 1. Optimization of Haloselective Cross-Coupling^a.

^aUnless otherwise noted, reactions were run using 0.1 mmol of 1a for 16 h at 27 °C and using a 1:1 Ni/ligand ratio.

^bConversions and ratios of 3a to 4a were determined by GC/MS and confirmed by ¹H NMR analysis of the crude reaction mixture.

^cValues in parentheses indicate the isolated yields on a 0.5 mmol scale of 1a.

^dA 1:2 Ni/ligand ratio and 2.5 mol % of Ru(bpy)₃(PF₆)₂ were used.