Tin-free Alternatives to the Barton-McCombie Deoxygenation of Alcohols to Alkanes Involving Reductive Electron Transfer

Authors

  • Ludwig Chenneberg Institut Parisien de Chimie Moléculaire (UMR CNRS 8232) UPMC Univ-Paris 06, Sorbonne Universités 4 Place Jussieu, C. 229, 75005 Paris, France
  • Cyril Ollivier Institut Parisien de Chimie Moléculaire (UMR CNRS 8232) UPMC Univ-Paris 06, Sorbonne Universités 4 Place Jussieu, C. 229, 75005 Paris, France;, Email: cyril.ollivier@upmc.fr

DOI:

https://doi.org/10.2533/chimia.2016.67

Keywords:

Alcohols, Deoxygenation, Electron transfer, Radicals, Reduction

Abstract

Echoing the recent celebration of the fortieth anniversary of the Barton-McCombie reaction, this review aims to explore another facet of radical processes for deoxygenation of alcohols by considering SET (single electron transfer) reduction of carboxylic ester, thiocarbonate and thiocarbamate derivatives. Various protocols have been developed relying on the use of organic and organometallic SET reagents, electrochemical conditions, photoinduced electron transfer processes and visible-light photoredox catalysis. Applications to the synthesis of molecules of interest provide a glimpse into the scope of these different approaches.

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Published

2016-02-24

Issue

Section

Scientific Articles