N-Alkylation of Amines with Alcohols Catalyzed by Manganese(II) Chloride or Bromopentacarbonylmanganese(I)

A manganese-catalyzed N-alkylation reaction of amines with alcohols via hydrogen autotransfer strategy has been demonstrated. The developed practical catalytic system including an inexpensive, nontoxic, commercially available MnCl2 or MnBr(CO) s as the metal salt and triphenylphosphine as a ligand provides access to diverse aromatic, heteroaromatic, and aliphatic secondary amines in moderate-to-high yields. In addition, this operationally simple protocol is scalable to the gram level and suitable for synthesizing heterocycles such as indole and resveratrol-derived amines known to be active for Alzheimer's disease.

Automated summary

A manganese-catalyzed N-alkylation reaction has been demonstrated, providing access to diverse secondary amines in moderate-to-high yields. The catalytic system is practical, scalable, and suitable for synthesizing heterocycles with potential activity against Alzheimer's disease.