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Synfacts 2019; 15(08): 0902
DOI: 10.1055/s-0039-1689840
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Radical-Driven Deoxygenation of Secondary Alcohols: The Barton–McCombie Reaction

Contributor(s):
Paul Knochel
,
Simon Graßl
Barton DH. R. * McCombie SW. * Imperial College London, UK
A New Method for the Deoxygenation of Secondary Alcohols.

J. Chem. Soc., Perkin Trans. 1 1975;
16: 1574-1585
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Further Information

Publication History

Publication Date:
18 July 2019 (online)

 
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Key words

deoxygenation - secondary alcohols - stannanes

Significance

The authors reported a very broadly applicable method for the deoxygenation of secondary alcohols, providing complex hydrocarbons in high yields. The alcohol thereby has to be activated by transforming it into its corresponding thioester.


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Comment

By using a radical mechanism and the favorable formation of an S–Sn bond, these thioesters can be deoxygenated. This concept has been revived in the Barton–McCombie decarboxylation (J. Chem. Soc., Chem. Commun. 1980, 15, 732).


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