Facile synthesis of 1,2-aminoalcohols via α-C–H aminoalkylation of alcohols by photoinduced hydrogen-atom transfer catalysis

Abstract

1,2-Aminoalcohols are common motifs found in a wide range of natural products and pharmaceutical compounds. Here we report a photocatalytic method for the direct conversion of readily available aliphatic alcohols into synthetically valuable 1,2-aminoalcohols. A dual catalytic system consisting of an acridinium photoredox catalyst and a cationic hydrogen-atom transfer (HAT) catalyst based on 1,4-diazabicyclo[2.2.2]octane (DABCO) enables an efficient and site-selective HAT from the α-C–H bonds of unprotected primary and secondary alcohols. The subsequent radical addition to a newly designed chiral N-sulfinyl α-iminoester afforded various 1,2-aminoalcohols, including enantiomerically enriched ones, under mild photochemical conditions with high atom and step economy.