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Selective Palladium‐Catalyzed Allenic C−H Bond Oxidation for the Synthesis of [3]Dendralenes
Author(s) -
Qiu Youai,
Posevins Daniels,
Bäckvall JanE.
Publication year - 2017
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.201706211
Subject(s) - allene , chemistry , moiety , palladium , ketone , aldehyde , phosphonate , sulfone , stereoselectivity , catalysis , substrate (aquarium) , double bond , organic chemistry , combinatorial chemistry , medicinal chemistry , oceanography , geology
A highly selective palladium‐catalyzed allenic C−H bond oxidation was developed, and it provides a novel and straightforward synthesis of [3]dendralene derivatives. A variety of [3]dendralenes with diverse substitution patterns are accessible with good efficiency and high stereoselectivity. The reaction tolerates a broad substrate scope containing various functional groups on the allene moiety, including ketone, aldehyde, ester, and phenyl groups. Also, a wide range of olefins with both electron‐donating and electron‐withdrawing aryls, acrylate, sulfone, and phosphonate groups are tolerated.