Manganese N,N,N-pincer complex-catalyzed epoxidation of unactivated aliphatic olefins

Abstract

A practical in situ generated manganese(II) catalyst system with the commercially available bis(2-picolyl) amine ligand enables epoxidation of terminal aliphatic olefins in good yields with tert-butyl hydroperoxide as oxidant. Crystallization experiments revealed the formation of two manganese solvent complexes with MeCN and H₂O, respectively. Furthermore, a detailed investigation of the quinoline additive identified its crucial role in this transformation as being both essential for the epoxide formation while simultaneously being detrimental to its stability.