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Durham University

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Publication details for Prof. AnnMarie C. O'Donoghue

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

Author(s) from Durham


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.