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Stille Coupling

(Stille Cross-Coupling, Stille Reaction)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr603

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Stille Coupling. Comprehensive Organic Name Reactions and Reagents. 603:2677–2685.

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

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The palladium-catalyzed cross-coupling reaction between an organostannane and an organic halide or its equivalent (e.g., acetate, triflate, and boronate) without a sp3-hybridized β-hydrogen is generally known as the Stille coupling. It has been reported that the presence of a β-(2-pyridyl) group may change the migratory aptitude, owing to the chelation of the pyridyl group with tin or palladium. In addition, the Stille coupling often requires a phosphorus ligand and copper(I) iodide. Another series of catalysts consisting of palladium and phosphinous acid for the Stille coupling in aqueous solution without an organic co-solvent have been developed recently. In particular, the recently developed proazaphosphatranes in the form of P(RNCH2CH2)3N (R = benzyl, iso-butyl) facilitate the coupling of a variety of aryl chlorides with organotin compounds, with the compatibility for functional groups. Moreover, the Stille coupling can also be used for the preparation of carbonyl compounds in the presence of carbon monoxide or through the direct reaction with acyl halides, a reaction known as the carbonylative Stille cross-coupling. However, this reaction also holds some intrinsic drawbacks so that it is gradually replaced by other coupling reactions. This reaction has very broad application in organic synthesis.


  • organostannanes;
  • palladium;
  • phosphinous acid;
  • copper (I) iodide