Hojoon Park1, Yang Li1, Jin-Quan Yu1. 1. Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Abstract
PdII -catalyzed C(sp3 )-H olefination of weakly coordinating native amides is reported. Three major drawbacks of previous C(sp3 )-H olefination protocols, 1) in situ cyclization of products, 2) incompatibility with α-H-containing substrates, and 3) installation of exogenous directing groups, are addressed by harnessing the carbonyl coordination ability of amides to direct C(sp3 )-H activation. The method enables direct C(sp3 )-H functionalization of a wide range of native amide substrates, including secondary, tertiary, and cyclic amides, for the first time. The utility of this process is demonstrated by diverse transformations of the olefination products.
PdII -catalyzed n class="Species">C(sp3 )-Holefination of weakly coordinating native amides is reported. Three major drawbacks of previous C(sp3 )-Holefination protocols, 1) in situ cyclization of products, 2) incompatibility with α-H-containing substrates, and 3) installation of exogenous directing groups, are addressed by harnessing the carbonyl coordination ability of amides to direct C(sp3 )-H activation. The method enables direct C(sp3 )-H functionalization of a wide range of native amide substrates, including secondary, tertiary, and cyclic amides, for the first time. The utility of this process is demonstrated by diverse transformations of the olefination products.