Stille cross coupling

What is Stille cross coupling?

Stille cross coupling is a chemical reaction used to synthesize organic compounds by coupling aryl or vinyl halides with organostannanes. The reaction was developed by J. K. Stille in the 1980s and has since become a widely used method in organic chemistry due to its high efficiency and wide substrate scope..

Stille cross coupling
Stille cross coupling

The reaction mechanism of Stille coupling involves the formation of a complex between the organostannane and a palladium catalyst, which then undergoes oxidative addition to form a palladium-carbon bond. The aryl or vinyl halide is then introduced and undergoes a reductive elimination reaction to form the desired coupling product..

One of the main advantages of Stille coupling is its compatibility with a wide range of functional groups, including alkyl, aryl, and vinyl groups. This makes it a useful method for synthesizing a wide range of organic compounds, including pharmaceuticals, agrochemicals, and materials..

Stille coupling is also highly efficient, with high yield and good selectivity. It is typically performed under mild reaction conditions, which makes it suitable for synthesizing sensitive and labile compounds..

There are several variations of Stille coupling that have been developed to improve its efficiency and scope, including the use of different palladium catalysts and the use of modified reaction conditions. For example, the use of palladium on carbon (Pd/C) as a catalyst has been shown to improve the yield and selectivity of Stille coupling..


Stille coupling is a powerful tool for synthesizing a wide range of organic compounds and has become an essential method in organic chemistry..