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.

doi:10.1039/c2sc22137c

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.

Authors

C.J. Collett

R.S. Massey

O.R. Maguire

A.S. Batsanov

Professor Ann O'Donoghue annmarie.odonoghue@durham.ac.uk
Professor

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