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The McMurry reductive coupling reaction is an organic reaction in which two ketone or aldehyde groups are coupled to an alkene in the presence of titanium(III) chloride and a reducing agent [61, 62]. As an example, intramolecular reductive McMurry coupling reactions of bis(formylphenoxy)-substituted calix[4]arenediols mediated by titanium(IV) chloride and activated zinc followed by cyclocondensation of the diols with tetra- and penta(ethylene glycol) bistosylates provided stilbene- and crown ether-bridged calix[4]arenes. For the synthesis of stilbenes, some authors use the Suzuki–Miyaura coupling that is the reaction of an aryl- or vinylboronic acid with an aryl or vinyl halide catalyzed by a palladium(0) complex (Figure 1.1) [63].

A combination of alkali metal salts, particularly potassium chloride, with low-valent titanium reagents generated from titanium chlorides with lithium or magnesium in either THFor DME areeffe ctivereagents for stereoselective McMurry coupling reactions of aldehydes and ketones to substituted alkenes (Figure 1.11).

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