Mn-catalyzed ring-opening and alkylation of epoxides with alcohols for accessing β-alkylated secondary alcohols via borrowing hydrogen

Abstract

Reported herein is a well-defined bidentate geometry-constrained pyridyl hydrazone manganese complex for an efficient and highly selective ring-opening and alkylation of epoxides with alcohols to deliver β-alkylated secondary alcohols. A broad substrate scope was shown, involving aromatic and aliphatic epoxides with both (hetero)aromatic and aliphatic primary/secondary alcohols. Control and labelling experiments showed that the reaction underwent a reductive ring-opening of epoxide with alcohol and β-alkylation of alcohol via a borrowing hydrogen pathway.