Scheme 3. Substrate Scope of Aryl Chlorides for the Nickel-Catalyzed Reductive Cross-Coupling^,

Reaction conditions: aryl chloride (0.75 mmol), alkyl bromide (0.94 mmol), NiI₂·xH₂O (0.054 mmol), ligand 6 (0.05 mmol), pyridine (0.05 mmol), zinc dust (>10 μm, 1.5 mmol), and DMPU (3 mL) were assembled on the bench in a 1 dram vial and heated for 18–23 h under air.

Yields are of isolated and purified product.

Average of two runs.

Used 1.0 equiv alkyl bromide (0.75 mmol).

Technical grade 1-chloronaphthalene was used (87:13 1-chloronaphthalene/2-chloronaphthalene).