Free Amino Group-Directed γ-C(sp3)-H Arylation of α-Amino Esters with Diaryliodonium Triflates by Palladium Catalysis

Abstract

Free amino group-directed C(sp³)-H functionalization of aliphatic amines is a fundamental challenge in synthetic organic chemistry. Also, the NH₂-directed C(sp³)-H functionalization of α-amino acids and their derivatives remains barely explored. With palladium as the catalyst and Ag₂O as the additive, we developed the first NH₂-directed γ-C(sp³)-H arylation of α-amino esters with diaryliodonium triflates for the construction of synthetically useful γ-aryl-α-amino esters, and the result of the KIE study suggested that the catalytic reaction involved an irreversible C-H cleavage as the rate-determining step.