Illustrated Glossary of Organic Chemistry

Stille reaction (Stille coupling): A coupling reaction between two sp² carbons, in which one carbon is bonded to a trialkyltin group, and the other carbon is bonded to a leaving group (chloride, bromide, iodide, or sulfonate), all in the presence of a Pd⁰ catalyst.

In this example Stille coupling reaction, phenyltrimethyltin couples with 2-iodofuran in the presence of Pd(PPh₃)₄ catalyst. The reaction product is 2-phenylfuran.