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C−H Coupling Reactions Directed by Sulfoxides: Teaching an Old Functional Group New Tricks
Author(s) -
Pulis Alexander P.,
Procter David 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.201601540
Subject(s) - electrophile , chemistry , nucleophile , sulfoxide , sulfonium , metalation , combinatorial chemistry , surface modification , functional group , reactivity (psychology) , catalysis , organic chemistry , salt (chemistry) , medicine , polymer , alternative medicine , pathology
Sulfoxides are classical functional groups for directing the stoichiometric metalation and functionalization of C−H bonds. In recent times, sulfoxides have been given a new lease on life owing to the development of modern synthetic methods that have arisen because of their unique reactivity. They have recently been used in catalytic C−H activation proceeding via coordination of an internal sulfoxide to a metal or through the action of an external sulfoxide ligand. Furthermore, sulfoxides are able to capture nucleophiles and electrophiles to give sulfonium salts, which subsequently enable the formation of C−C bonds at the expense of C−H bonds. This Review summarizes a renaissance period in the application of sulfoxides arising from their versatility in directing C−H functionalization.