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.
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.
|Full text:||(AM) Accepted Manuscript|
Download PDF (749Kb)
|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|
Save or Share this output
|Look up in GoogleScholar|