Synthesis of Amides and Esters by Pd0-Catalyzed Carbonylative C(sp3)-H Activation

Angewandte Chemie
Tomáš ČarnýOlivier Baudoin

Abstract

The 1,4-Pd shift strategy allows the functionalization of remote C-H bonds that are difficult to reach directly. We report a domino reaction proceeding via C(sp3)-H activation, 1,4-Pd shift and amino- or alkoxycarbonylation, which generates a variety of amides and esters bearing a quaternary β carbon. Mechanistic studies showed that the aminocarbonylation of the σ-alkylpalladium intermediate arising from Pd shift is fast using PPh3 as the ligand, and leads to the amide rather than the previously reported indanone product.

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