Mechanistic elucidation of monoalkyltin(iv)-catalyzed esterification.

Catalysis Science & Technology
Lukas A WolzakTies J Korstanje

Abstract

Monoalkyltin(iv) complexes are well-known catalysts for esterification reactions and polyester formation, yet the mode of operation of these Lewis acidic complexes is still unknown. Here, we report on mechanistic studies of n-butylstannoic acid in stoichiometric and catalytic reactions, analyzed by NMR, IR and MS techniques. While the chemistry of n-butyltin(iv) carboxylates is dominated by formation of multinuclear tin assemblies, we found that under catalytically relevant conditions only monomeric n-BuSn(OAc)3 and dimeric (n-BuSnOAc2OEt)2 are present. Density functional theory (DFT) calculations provide support for a mononuclear mechanism, where n-BuSn(OAc)3 and dimeric (n-BuSnOAc2OEt)2 are regarded as off-cycle species, and suggest that carbon-oxygen bond breaking is the rate-determining step.

References

Jul 5, 2003·Chemical Communications : Chem Comm·Bernard JousseaumeThierry Toupance
May 19, 2004·Accounts of Chemical Research·Junzo Otera
May 8, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Evan CrawfordJ Scott McIndoe
Jan 20, 2017·Journal of the American Chemical Society·Helena LundbergHans Adolfsson

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