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Tandem Csp3–Csp2 cross-coupling. Numbers in parentheses are ratios of 3:4 after the first coupling. Conditions: (a) 1 (1.0 equiv, 0.5 mmol), alkylsilicate (1.2 equiv), NiCl2·dme (2.5 mol %), Ru(bpy)3(PF6)2 (2 mol %), and phen (5 mol %) DMF (0.1 M), blue LEDs, rt, 24 h; (b) alkylsilicate (1.2 equiv), [Ni(dtbbpy)(H2O)4]Cl2 (5 mol %), and Ru(bpy)3(PF6)2 (2 mol %), DMF (0.1 M), blue LEDs, rt, 24 h.
