Reductive Deoxygenation of Alcohols: Catalytic Methods Beyond Barton-McCombie Deoxygenation

Deoxygenation is an extensively studied field in organic chemistry, and over the last decades many methods such as the Barton–McCombie deoxygenation reaction or deoxygenation with alkali metals in liquid ammonia have been established. Within this microreview, we discuss different strategies for the...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-11, Vol.2013 (31), p.7017-7027
Main Authors: Herrmann, Josef M., König, Burkhard
Format: Article
Language:English
Subjects:
Alcohols
Alkali metals
Ammonia
Chemoselectivity
Deoxygenation
Heterogeneous catalysis
Homogeneous catalysis
Liquid ammonia
Methods
Organic chemistry
Synthetic methods
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Summary:Deoxygenation is an extensively studied field in organic chemistry, and over the last decades many methods such as the Barton–McCombie deoxygenation reaction or deoxygenation with alkali metals in liquid ammonia have been established. Within this microreview, we discuss different strategies for the chemoselective catalytic deoxygenation of alcohols with special attention to their scope and limitations. The deoxygenation of derivatives of alcohols and their direct deoxygenation as step‐economic alternative are covered with current examples. Catalytic methods can serve as convenient and economic alternatives for established methods in the reduction of carbon–oxygen single bonds. The selective reductive removal of hydroxy groups becomes an increasingly important transformation in synthesis as more biomass‐derived starting materials, often highly oxidized and functionalized, will be used in the future.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300657