Metal-Catalyzed Carbon-Carbon Bond Cleavage of Unstrained Alcohols

The functionalization of molecules by cleaving inert carbon-carbon single bonds is regarded as a great synthetic challenge due to their inherent stability. In recent years, significant progress has been made in the activation of small rings relying on the release of strain energy. By contrast, the n...

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Bibliographic Details
Published in:Chemical reviews 2021-01, Vol.121 (1), p.300-326
Main Authors: Lutz, Marius D R, Morandi, Bill
Format: Article
Language:English
Subjects:
Alcohols
Carbon
Chemical bonds
Cleavage
Covalent bonds
Ductile-brittle transition
Transition metals
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Summary:The functionalization of molecules by cleaving inert carbon-carbon single bonds is regarded as a great synthetic challenge due to their inherent stability. In recent years, significant progress has been made in the activation of small rings relying on the release of strain energy. By contrast, the number of catalytic methodologies for the activation of unstrained carbon-carbon single bonds is still limited. This review focuses on the recent developments in transition-metal-catalyzed cleavage of C-C bonds in unstrained alcohols via β-carbon elimination. Emphasis is placed on the mechanistic aspects of the discussed transformations and their applications to the deconstruction and reorganization of molecules.
ISSN:0009-2665
1520-6890
DOI:10.1021/acs.chemrev.0c00154