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Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions: role of the N-aryl substituent

Collett, C.J.; Massey, R.S.; Maguire, O.R.; Batsanov, A.S.; O'Donoghue, A.C.; Smith, A.D.

Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions: role of the N-aryl substituent Thumbnail


Authors

C.J. Collett

R.S. Massey

O.R. Maguire

A.S. Batsanov

A.D. Smith



Abstract

The in situ observation, isolation and reversible formation of intermediate 3-(hydroxybenzyl)azolium salts derived from NHC addition to a range of substituted benzaldehydes is probed. Equilibrium constants for the formation of these 3-(hydroxybenzyl)azolium salts, as well as rate constants of hydrogen–deuterium exchange (kex) at C(α) of these intermediates for a range of N-aryl triazolinylidenes is reported. These combined studies give insight into the preference of N-pentafluorophenyl NHCs to participate in benzoin and Stetter reaction processes.

Citation

Collett, C., Massey, R., Maguire, O., Batsanov, A., O'Donoghue, A., & Smith, A. (2013). Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions: role of the N-aryl substituent. Chemical Science, 4(4), 1514-1522. https://doi.org/10.1039/c2sc22137c

Journal Article Type Article
Acceptance Date Jan 4, 2013
Publication Date Apr 1, 2013
Deposit Date May 16, 2013
Publicly Available Date Feb 15, 2016
Journal Chemical Science
Print ISSN 2041-6520
Electronic ISSN 2041-6539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 4
Issue 4
Pages 1514-1522
DOI https://doi.org/10.1039/c2sc22137c

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