Photoinduced radical generation and trapping by acrylonitrile of N-Boc secondary amine and N-Boc N-methyl α-amino acid ester at α-position using two-molecule photoredox catalysts

Abstract

The photoreaction of an N-Boc secondary amine and N-Boc N-methyl α-amino acid ester with acrylonitrile using inexpensive two-molecule photoredox catalysts results in the production of α-alkylated amine through the generation of an α-carbamy radical under mild conditions. In particular, this mothed leads to a regioselective modification of N-Boc N-methyl α-amino acid ester with the retention of α-chirality through the generation of the less stable primary α-carbamyl radical.

Keywords

• Two-molecule photoredox catalyst
• Oxidation of N-Boc secondary amine
• Radical cation of N-Boc secondary amine
• N-Boc N-methyl α-amino acid ester
• Generation of α-carbamyl radical