Free Amino Group-Directed gamma-C(sp(3))-H Arylation of alpha-Amino Esters with Diaryliodonium Triflates by Palladium Catalysis

摘要

Free amino group-directed C(sp(3))-H functionalization of aliphatic amines is a fundamental challenge in synthetic organic chemistry. Also, the NH2-directed C(sp(3))-H functionalization of alpha-amino acids and their derivatives remains barely explored. With palladium as the catalyst and Ag2O as the additive, we developed the first NH2-directed gamma-C(sp(3))-H arylation of alpha-amino esters with diaryliodonium triflates for the construction of synthetically useful gamma-aryl-alpha-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.