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Please login to access the full content or check if you have access via Method 3: Reductive Coupling of Ketones with Esters in the Presence of Titanium Complexes (The McMurry Coupling)

DOI: 10.1055/sos-SD-032-00627

Milata, V.; Rádl, S.; Voltrová, S.Science of Synthesis, (200832661.

In the McMurry reaction, a carbonyl compound is coupled in the presence of titanium compounds and a reducing agent to form an alkene. A similar intramolecular McMurry coupling of oxo esters is regarded as a formal intramolecular alkenation reaction. The McMurry reaction is useful for the preparation of furans[‌189‌] and benzofurans,[‌190‌,‌191‌] but the intermolecular mixed McMurry-type coupling reaction of a ketone with an ester is generally inefficient, giving mainly the coupled ketone, with only low yields of the required mixed product.