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Utilizing Carbonyl Coordination of Native Amides for Palladium‐Catalyzed C(sp 3 )−H Olefination
Author(s) -
Park Hojoon,
Li Yang,
Yu JinQuan
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201906075
Subject(s) - amide , palladium , catalysis , chemistry , surface modification , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry
Pd II ‐catalyzed C(sp 3 )−H olefination of weakly coordinating native amides is reported. Three major drawbacks of previous C(sp 3 )−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(sp 3 )−H activation. The method enables direct C(sp 3 )−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.