Table 1.

Nickel-catalyzed reductive dimerization of 2-chloropyridines.^a

Entry	3	Yield (%)b
1		90
2c		70
3d		86

^aReaction conditions: 2a (4.99g, 29.4 mmol), NiBr₂·3H₂O (401 mg, 1.47 mmol), DMF (20 mL), and manganese powder (−325 mesh, 3.30 g, 60.0 mmol) were heated under argon for 20 h.

^bYield of isolated and purified product.

^cReaction run on 15.0 mmol scale with 2b.

^dReaction run on 15.0 mmol scale with 2c with 0.2 mol% NiBr₂·3H₂O for 18 h.