Bisphenols from Furfurals by Organocatalysis and Gold Catalysis

A. Stephen K. Hashmi; Michael Wölfle; J. Henrique Teles; Wolfgang Frey

doi:10.1055/s-2007-982569

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Synlett 2007(11): 1747-1752
DOI: 10.1055/s-2007-982569

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Bisphenols from Furfurals by Organocatalysis and Gold Catalysis

A. Stephen K. Hashmi*^a,, Michael Wölfle^a, J. Henrique Teles*^b, Wolfgang Frey^a
^a Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
Fax: +49(711)6854330; e-Mail: hashmi@hashmi.de;
^b BASF Aktiengesellschaft, 67056, Ludwigshafen, Germany
Fax: +49(621)606656359; e-Mail: henrique.teles@basf.com;

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Publication History

Received 5 March 2007
Publication Date:
25 June 2007 (online)

Abstract
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Abstract

Four different benzoins were formed from furfurals by organocatalysis with heterocyclic carbenes, reduced to the diols and converted into propargyl ethers. The gold-catalyzed cyclization exclusively gave bisphenols of the bisdihydroisobenzofuran type.

Key words

alkynes - furans - gold catalysis - organocatalysis - triazolium salts

References and Notes

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1

New address: A. S. K. Hashmi, Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.