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Dupuy S, Crawford L, Bühl M, et al. The gold(i)-catalysed protodecarboxylation mechanism. Chemistry. 2015;21(8):3399-408doi: 10.1002/chem.201405716.
Dupuy, S., Crawford, L., Bühl, M., & Nolan, S. P. (2015). The gold(i)-catalysed protodecarboxylation mechanism. Chemistry (Weinheim an der Bergstrasse, Germany), 21(8), 3399-408. https://doi.org/10.1002/chem.201405716
Dupuy, Stéphanie, et al. "The gold(i)-catalysed protodecarboxylation mechanism." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,8 (2015): 3399-408. doi: https://doi.org/10.1002/chem.201405716
Dupuy S, Crawford L, Bühl M, Nolan SP. The gold(i)-catalysed protodecarboxylation mechanism. Chemistry. 2015 Feb 16;21(8):3399-408. doi: 10.1002/chem.201405716. Epub 2015 Jan 07. PMID: 25580591.
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Chemistry. 2015 Feb 16;21(8):3399-408. doi: 10.1002/chem.201405716. Epub 2015 Jan 07.

The gold(i)-catalysed protodecarboxylation mechanism.

Chemistry (Weinheim an der Bergstrasse, Germany)

Stéphanie Dupuy, Luke Crawford, Michael Bühl, Steven P Nolan

Affiliations

  1. EastCHEM, School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST (UK).

PMID: 25580591 DOI: 10.1002/chem.201405716

Abstract

A mechanistic study of the gold-catalysed protodecarboxylation is described. Each reaction step has been investigated experimentally and computationally. More specifically, the activation parameters for the decarboxylation step have been determined through kinetic studies. Further experimental studies on the hydrolysis of the arylgold intermediate have revealed that the protodeauration can become competitive with the decarboxylation process at high conversions. This switch in rate-limiting step has been shown to be pKa -dependent. These studies have been supported by DFT calculations and permit a better understanding of which prevalent features of the reaction mechanism account for the decarboxylation process.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: N-heterocyclic carbenes; decarboxylation; gold; mechanism; protodeauration

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