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.

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
• Public URL: https://durham-repository.worktribe.com/output/1453154