Tin has been used for many purposes over several centuries. With the past several decades, the area of tin catalysis has seen a renaissance. Alkyl tins, or more commonly known as organostannanes, have become part of the chemist′s toolbox for a wide range of synthetic transformations. Stannoxanes, often organostannanes that incorporate oxygen atoms, are synthetically useful transformations and have been known to catalyze transesterification of lower alkyl groups with very low catalyst loading and therefore can be considered high efficiency (e.g. Otera′s tin catalysts). Similarly, organotins have found widespread use radical proton donors, the most common of which is tributyltin hydride. However, the utility of tin in research arenas gained significant momentum with the development of cross coupling reactions (known as a Stille coupling) involving an aryl or alkenyl halide or pseudohalide and a trialkyl organostannane substituted with a pendant ligand that will undergo transmetallation and ultimately be coupled to the alkenyl halide or pseudohalide.
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