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Synthesis 1980; 1980: 425-452
DOI: 10.1055/s-1980-29046

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
 
 
The Hydrogenolysis of Organic Halides
 
A. R. Pinder*
*Department of Chemistry, Clemson University, Clemson, South Carolina 29631, U.S.A.

The hydrogenolysis (dehalogenation, reductive dehalogenation) of organic halides is an important, well-established reaction which is frequently used in organic synthesis. Recently, new reducing agents have become available and many of these reagents have been applied to the hydrogenolysis of the carbon-halogen bond with notable success. In this review the entire field is surveyed and typical examples are described. The subject matter is treated from the viewpoints of the nature of the halogen atom, its structural environment in the molecule, and the reducing conditions capable of effecting hydrogenolysis. Numerous examples are described - some with experimental details - to enable the reader to select the most advantageous conditions pertinent to a desired dehalogenation reaction. 1 . Introduction 2. Scope of the Review 3. General Observations 4. Hydrogenolysis of Structural Types 4.1. Unactivated Alkyl and Cycloalkyl Halides 4.2. Activated Alkyl and Cycloalkyl Halides 4.3. Allylic and Benzylic Halides 4.4. Vinyl and Aryl Halides 4.5. Cyclopropyl Halides 5. Addenda 6. Conclusions

 
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