Utilizing Carbonyl Coordination of Native Amides for Palladium-Catalyzed C(sp3 )-H Olefination
Hojoon Park1, Yang Li1, Jin-Quan Yu1
1Department 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.
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