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Oxidative Heck Arylation for the Stereoselective Synthesis of Tetrasubstituted Olefins Using Nitroxides as Oxidants
Author(s) -
He Zhiheng,
Kirchberg Sylvia,
Fröhlich Roland,
Studer Armido
Publication year - 2012
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.201108211
Subject(s) - stereoselectivity , chemistry , oxidative phosphorylation , aryl , methyl acrylate , catalysis , heck reaction , organic chemistry , acrylate , combinatorial chemistry , palladium , polymer , alkyl , biochemistry , monomer , copolymer
One, two, and three! Nitroxides and dioxygen serve as oxidants in highly stereoselective oxidative Pd‐catalyzed Heck arylations in which aryl boronic acids are used to synthesize triarylalkyl‐substituted olefins. The reactions occur under very mild conditions at room temperature. As an example, the threefold sequential arylation of methyl acrylate is the crucial step in the stereoselective synthesis of Z ‐Tamoxifen.