McMurry Reaction

This reductive coupling involves two steps. The coupling is induced by single electron transfer to the carbonyl groups from alkali metal (see Pinacol Coupling), followed by deoxygenation of the 1,2-diol with low-valent titanium to yield the alkene.

The McMurry Reaction works well to produce symmetric products or rings:

Mechanism of the McMurry Reaction

Recent Literature

A New Approach to the Preparation of 1,3,4-Triarylpyrroles
D. X. Zeng, Y. Chen, Synlett, 2006, 490-492.

Insights into the General and Efficient Cross McMurry Reactions between Ketones
X.-F. Duan, J. Zeng, J.-W. Lü, Z.-B. Zhang, J. Org. Chem., 2006, 71, 9873-9876.