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

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

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.

Item Type:Article
Full text:(AM) Accepted Manuscript
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Status:Peer-reviewed
Publisher Web site:http://dx.doi.org/10.1039/c2sc22137c
Date accepted:04 January 2013
Date deposited:15 February 2016
Date of first online publication:April 2013
Date first made open access:No date available

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