Photoinduced decarboxylative carbocation generation from α-amino acid using Selectfluor

Abstract

A photoredox system employing 9,10-diphenylanthracene (9,10-DPA) as an electron donor and Selectfluor as both an electron acceptor and oxidant facilitated the conversion of α-amino acids into α-amino alcohols through the formation of carbocations via photoinduced decarboxylation. Various N-protected α-amino acids and dipeptide were successfully converted into their corresponding α-amino alcohols under mild conditions. The reaction proceeded via PET-promoted decarboxylation of N-protected α-amino acids using 9,10-DPA and Selectfluor to generate alkyl radicals that were subsequently oxidized by Selectfluor to form carbocations.