Synlett 2015; 26(19): 2673-2678
DOI: 10.1055/s-0035-1560648
letter
© Georg Thieme Verlag Stuttgart · New York

Indium Versus Gold Catalysis in Dehydrative Reactions with Allylic Alcohols

Stacey Webster, Louise Schaefer, Graeme Barker, Ai-Lan Lee*
  • Institute of Chemical Sciences, School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh EH14 4AS, UK   eMail: A.Lee@hw.ac.uk
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Publikationsverlauf

Received: 17. August 2015

Accepted after revision: 14. September 2015

Publikationsdatum:
02.Oktober 2015 (eFirst)

Abstract

Indium(III) chloride can be used as a cheaper alternative to gold(I) complexes as a catalyst in dehydrative reactions with allylic alcohols. There is often an improvement in yield and, in particular, indium(III) chloride outperforms gold(I) as a catalyst in chemoselective reactions. For example, substrates with pendent alkyne or alkene groups react poorly under gold(I) catalysis, but are better tolerated under indium(III) chloride catalysis.

Supporting Information

 
  • References and Notes


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  • 18 See ref. 5a for control experiments proving that the reaction is not catalyzed by Brønsted acid, and ref. 5d for detailed mechanistic investigations.