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

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Date
2013
Author
Collett, Christopher J.
Massey, Richard S.
Maguire, Oliver R.
Batsanov, Andrei S.
O'Donoghue, AnnMarie C.
Smith, Andrew D.
Keywords
Heterocyclic carbene
Thiazolium salts
Michael addition
Triazolium salts
Umpolung reaction
Nucleophilic carbenes
Breslow intermediate
Alpha,beta-unsaturated aldehydes
Thiamine action
Homoenolate equivalents
QD Chemistry
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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 (k(ex)) at C(alpha) 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 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 , vol. 4 , no. 4 , pp. 1514-1522 . https://doi.org/10.1039/c2sc22137c
Publication
Chemical Science
Status
Peer reviewed
DOI
https://doi.org/10.1039/c2sc22137c
ISSN
2041-6520
Type
Journal article
Rights
This is an open access article. This journal is (c) The Royal Society of Chemistry 2013
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/3509

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