Scheme 2.

Scope of Methylation^a

^a Conditions: alkylpyridinium salt (1.0 mmol, 1.0 equiv), NiBr₂(1-bpp) (10 mol %), Mn (2.0 equiv), CH₃I (1.2 equiv), DMA (5 mL), rt, 1 h. Average yield of duplicate experiments (±8%), unless noted otherwise. ^b Single experiment. ^c 24 h. ^d Diastereomeric ratio (dr) of crude reaction mixture determined by ¹H NMR. ^e Glassware was not dried. ^f Minimal precautions to protect from air and moisture. See Supporting Information.