Issue 4, 2013
From the journal:

Chemical Science

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

Christopher J. Collett,a   Richard S. Massey,b   Oliver R. Maguire,b   Andrei S. Batsanov,b   AnnMarie C. O'Donoghue*b  and  Andrew D. Smith*a  

* Corresponding authors

a EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, UK
E-mail: ads10@st-andrews.ac.uk

b Department of Chemistry, University Science Laboratories, Durham University, South Road, Durham, UK
E-mail: annmarie.odonoghue@durham.ac.uk

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.

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

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Article information

DOI
https://doi.org/10.1039/C2SC22137C
Article type
Edge Article
Submitted
03 Dec 2012
Accepted
04 Jan 2013
First published
04 Jan 2013
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2013,4, 1514-1522

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

C. J. Collett, R. S. Massey, O. R. Maguire, A. S. Batsanov, A. C. O'Donoghue and A. D. Smith, Chem. Sci., 2013, 4, 1514 DOI: 10.1039/C2SC22137C

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