Mechanistic elucidation of monoalkyltin(iv)-catalyzed esterification

Lukas A. Wolzak, Joen J. Hermans, Folkert de Vries, Keimpe J. van den Berg, Joost N.H. Reek*, Moniek Tromp, Ties J. Korstanje*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

7 Citaten (Scopus)
120 Downloads (Pure)

Samenvatting

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 ofn-butylstannoic acid in stoichiometric and catalytic reactions, analyzed by NMR, IR and MS techniques. While the chemistry ofn-butyltin(iv) carboxylates is dominated by formation of multinuclear tin assemblies, we found that under catalytically relevant conditions only monomericn-BuSn(OAc)3and dimeric (n-BuSnOAc2OEt)2are present. Density functional theory (DFT) calculations provide support for a mononuclear mechanism, wheren-BuSn(OAc)3and dimeric (n-BuSnOAc2OEt)2are regarded as off-cycle species, and suggest that carbon-oxygen bond breaking is the rate-determining step.

Originele taal-2English
Pagina's (van-tot)3326-3332
Aantal pagina's7
TijdschriftCatalysis Science and Technology
Volume11
Nummer van het tijdschrift10
DOI's
StatusPublished - 21-mei-2021

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