3.7.4 Stille Coupling

The palladium-catalyzed C-C cross-coupling reaction of organotin reagents with electrophiles to give dienes is called ‘Stille Coupling' although Stille and Migita independently investigated this reaction (Scheme 3). The main advantage of this method is that a lot of functional groups like aldehydes, ketones, esters, nitriles, amines as well as alcohols are tolerated. In comparison to Suzuki coupling no base is needed. Therefore, organometallic compounds having tin as well as boron can be coupled selectively via tin. However, toxicity concerns are the major disadvantage of the cross-coupling of organostannanes. Both inter- and intramolecular reactions have been explored and widely applied in the synthesis of complex molecules.

Scheme 9

Scheme 10