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Updated: May 30, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-catalyzed dehydrostannylation of n-alkyltin trichlorides
Yves Cabon1, Robertus J M Klein Gebbink, Berth-Jan Deelman
1ARKEMA Vlissingen B.V., P.O. Box 70, NL-4380, AB Vlissingen, The Netherlands.
Abstract:
[Pd(PPh(3))(4)] catalyzes the dehydrostannylation of n-alkyltin trichlorides into HSnCl(3)(THF)(n) and isomers of the corresponding alkene. The reaction mechanism involves oxidative addition of the Sn-C bond followed by β-H elimination from the resulting n-alkylpalladium trichlorostannyl species. Rate-determining reductive elimination of HSnCl(3) from cis-[PdH(SnCl(3))(PPh(3))(2)] completes the catalytic cycle. Organotin trichlorides without β-H atoms either do not react or undergo thermal disproportionation. These results are relevant to understand some of the problems associated with the use of monoalkyltin compounds as coupling partner in Stille-type cross-coupling reactions as well as with the catalytic hydrostannylation of 1-alkenes to monoalkyltin trichlorides.
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