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McMurry Coupling

(McMurry Reaction)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr418

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. McMurry Coupling. Comprehensive Organic Name Reactions and Reagents. 418:1860–1865.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

McMurry has started the application of the low-valent titanium as reducing agent for several functional group and studied the scope of coupling of the carbonyl groups using LiAlH4, LiBH4, etc. in combination with TiCl3 or TiCl4 is generally known as the McMurry coupling or McMurry reaction. The combination of TiCl3 and Zn/Cu couple in DME or TiCl3-Li in DME is known as the McMurry reagent. This reaction generally gives trans-olefins but sometimes contaminated with pinacol. The study finds the formation of the predominant cis-stilbene from acetophenone under the McMurry coupling condition is due to the π -π preassociation. This coupling reaction has been further modified to enhance the chemoselectivity and diastereoselectivity. This reaction is useful in the preparation of olefins.

Keywords:

  • titanium;
  • trans-olefins;
  • cis-stilbene;
  • pinacol