Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
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Gold-Catalysis: Reactions of Organogold Compounds with Electrophiles

A. Stephen K. Hashmi A C , Tanuja Dondeti Ramamurthi A , Matthew H. Todd B , Althea S.-K. Tsang A B and Katharina Graf A

A Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

B School of Chemistry, University of Sydney, NSW 2006, Australia.

C Corresponding author. Email: hashmi@hashmi.de

Australian Journal of Chemistry 63(12) 1619-1626 http://dx.doi.org/10.1071/CH10342
Submitted: 15 September 2010  Accepted: 18 October 2010   Published: 6 December 2010

Abstract

Different arylgold(i), one alkynylgold(i), and one vinylgold(i) triphenylphosphane complexes were subjected to electrophilic halogenation reagents. With N-chlorosuccinimid, N-bromosuccinimid, and N-iodosuccinimid as well as the Barluenga reagent, selectively halogenated compounds were obtained. Trifluoroacetic acid, as a source of protons, leads to a clean protodeauration. With N-fluorobenzenesulfonimide or Selectfluor, exclusively a homocoupling was observed. For the precursor of the vinylgold(i) complex, a similar oxidative coupling could be induced by gold(iii) chloride. Reactions with silicon or tin electrophiles failed.

Graphical Abstract Image


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