Volume 52, Issue 33 pp. 8510-8525
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Migratory Insertion of Alkenes into Metal–Oxygen and Metal–Nitrogen Bonds

Dr. Patrick S. Hanley

Dr. Patrick S. Hanley

Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, IL 61801 (USA)

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Prof. John F. Hartwig

Corresponding Author

Prof. John F. Hartwig

Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, IL 61801 (USA)

University of California, Department of Chemistry, 718 Latimer Hall, Berkeley, CA 94720 (USA)

Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, IL 61801 (USA)Search for more papers by this author
First published: 05 July 2013
Citations: 100

Graphical Abstract

In the middle of things: Recent work has shown that the insertions of unactivated alkenes into the metal–oxygen and metal–nitrogen bonds of metal alkoxo and metal amido complexes can occur as rapidly or more rapidly than insertions into metal–alkyl bonds. Studies on catalytic and stoichiometric reactions occurring through this increasingly common class of organometallic reactions are reviewed.

Abstract

The insertion of an unsaturated ligand into a MC or MH bond proceeds through migratory insertion, a fundamental organometallic reaction. Recent literature documents evidence of the migratory insertion of alkenes into an MO and MN bonds for alkene alkoxylation and alkene amination reactions, respectively. Herein we provide an overview of the literature and a perspective on how these recent experiments relate to classic experiments on CO and CN bond formation with alkene complexes of the late transition metals.

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