Table 2.

Aryl Halide Scope of Ni/Photoredox DCF^a,b

^aValues indicate yield of the isolated product. pin = 2,3-dimethylbutane-2,3-diol.

^bConditions unless otherwise noted: aryl halide (1 equiv, 0.5 mmol), 3 (1.2 equiv, 0.6 mmol), 2 (1.5 equiv, 0.75 mmol), [Ir(dFCF₃ppy)₂bpy]PF₆ (2 mol %, 0.010 mmol), Ni(bpy)Br₂ (5 mol %, 0.025 mmol), K₂HPO₄ (2 equiv, 1.0 mmol), THF (0.1 M), 16 h, irradiating with blue LEDs (6 W).

^cReaction time extended to 48 h.

^dNi(dtbbpy)Br₂ used as the Ni catalyst.

^eNi(phen)Br₂ used as the Ni catalyst.

^fIsolated yield as BF₃K salt.

^g1H NMR yield of boronate ester

^hReaction performed on 5 mmol scale of aryl halide.