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

J Org Chem

MOE Key Laboratory of Cluster Science, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering , Beijing Institute of Technology, Beijing 102488 , P. R. China.

Published: May 2019

Free amino group-directed C(sp)-H functionalization of aliphatic amines is a fundamental challenge in synthetic organic chemistry. Also, the NH-directed C(sp)-H functionalization of α-amino acids and their derivatives remains barely explored. With palladium as the catalyst and AgO as the additive, we developed the first NH-directed γ-C(sp)-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.

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http://dx.doi.org/10.1021/acs.joc.9b00605DOI Listing

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