Stille reaction
Abstract
Stille reaction is a palladium-catalyzed cross-coupling reaction between an aryl halide, vinyl halide or alkyl halide (R1-X, where X = I, Br or Cl) and an organostannane.
Keywords
Aryl halide, Vinyl halide, Alkyl halide, Organostannane, Cross coupling
Category
Organometallic catalysis
Mechanism
The catalytic reaction starts with the oxidative addition step between the palladium center and the organic halide (1). The resulting palladium(II) intermediate undergoes transmetallation with an organostannane to generate an alkylpalladium species (2). Finally, the reductive elimination leads to the desired product and the palladium(0) catalyst (3).
Recent review
Cordovilla, C.; Bartolomé, C.; Martinez-Ilarduya, J. M.; Espinet, P. The Stille reaction, 38 years later. ACS Catal. 2015, 5, 3040-3053.