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Branched Arylalkenes from Cinnamates: Selectivity Inversion in Heck Reactions by Carboxylates as Deciduous Directing Groups
Author(s) -
Tang Jie,
Hackenberger Dagmar,
Goossen Lukas J.
Publication year - 2016
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.201605744
Subject(s) - cinnamates , chemistry , aryl , heck reaction , organic chemistry , catalysis , halide , carboxylate , palladium , alkyl
A decarboxylative Mizoroki–Heck coupling of aryl halides with cinnamic acids has been developed in which the carboxylate group directs the arylation into its β‐position before being tracelessly removed through protodecarboxylation. In the presence of a copper/palladium catalyst, both electron‐rich and electron‐deficient aryl bromides and chlorides bearing numerous functionalities were successfully coupled with broadly available cinnamates, with selective formation of 1,1‐disubstituted alkenes. This reaction concept, in which the carboxylate acts as a deciduous directing group, ideally complements traditional 1,2‐selective Heck reactions of styrenes.