Organostannanes arylstannanes

Aryl halides react with a wide variety of aryl-, alkenyl- and alkylstan-nanes[548-550]. Coupling of an aryl tritlate with an arylstannane is a good preparative method for diaryls such as 688. The coupling of alkenylstannanes with alkenyl halides proceeds stereospecifically to give conjugated dienes 689. The allylstannane 690 is used for allylation[397,546,551-553]. Aryl and enol triflates react with organostannanes smoothly in the presence of LiCl[554]. 

The intramolecular coupling of organostannanes is applied to macrolide synthesis. In the zearalenone synthesis, no cyclization was observed between arylstannane and alkenyl iodide. However, intramolecular coupling take.s place between the alkenylstannane and aryl iodide in 706. A similar cyclization is possible by the reaction of the alkenylstannane 707 with enol triflate[579]. The coupling was applied to the preparation of the bicyclic 1,3-diene system 708[580]. 

Carbonylative cross-coupling reaction between triarylbismuth(V) compounds and organostannanes is smoothly catalyzed by PdCl2 under 1 atm CO at room temperature (Scheme 48) [34]. Not only arylstannanes, but also heteroaryl-, alkynyl-, and vinyltributylstannanes were employed efficiently. 

Coupling Reactions. The Pd(PhCN)2Cl2-catalyzed reaction of organostannanes such as l-alk3tnyl and arylstannanes afforded the corresponding homocoupling products (eqs 9 and 10). ... 

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