Issue 16, 2010
From the journal:

Dalton Transactions

A new mechanistic pathway under Sonogashira reaction protocol involving multiple acetyleneinsertions†

Roderick C. Jones,*a   Allan J. Canty,*a   Tom Caradoc-Davies,b   Noel W. Davies,c   Michael G. Gardiner,a   Philip J. Marriott,d   Christian P. G. Rühled  and  Vicki-Anne Tolhursta  

* Corresponding authors

a School of Chemistry, University of Tasmania, Hobart, Tasmania, Australia
E-mail: Allan.Canty@utas.edu.au
Fax: +61 3 62262858
Tel: +61 3 6226 2162

b Australian Synchrotron, Clayton, Victoria, Australia

c Central Science Laboratory, University of Tasmania, Hobart, Tasmania, Australia

d Australian Centre for Research on Separation Science (ACROSS), School of Applied Sciences, RMIT University, Melbourne, Victoria, Australia

Abstract

An unreported product outcome from an intended Sonogashira coupling is presented. The generality of this finding has been demonstrated by screening of a range of pre-catalysts. Mechanistic studies are consistent with the tetra-aryl benzene product forming by interception of the aryl halide oxidative addition intermediate by repeated acetylene insertion.

Graphical abstract: A new mechanistic pathway under Sonogashira reaction protocol involving multiple acetylene insertions

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Article information

DOI
https://doi.org/10.1039/C001109F
Article type
Communication
Submitted
19 Jan 2010
Accepted
19 Feb 2010
First published
04 Mar 2010

Dalton Trans., 2010,39, 3799-3801

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A new mechanistic pathway under Sonogashira reaction protocol involving multiple acetylene insertions

R. C. Jones, A. J. Canty, T. Caradoc-Davies, N. W. Davies, M. G. Gardiner, P. J. Marriott, C. P. G. Rühle and V. Tolhurst, Dalton Trans., 2010, 39, 3799 DOI: 10.1039/C001109F

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