Synthesis 2008(17): 2707-2718  
DOI: 10.1055/s-2008-1067227
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalysis: Reactions of Furandialkynes

A. Stephen K. Hashmi*, Elisabeth Enns, Tanja M. Frost, Sascha Schäfer, Wolfgang Frey, Frank Rominger
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Fax: +49(6221)544205; e-Mail: hashmi@hashmi.de;
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Publikationsverlauf

Received 21 January 2008
Publikationsdatum:
13. August 2008 (online)

Abstract

Six furandialkynes were prepared and investigated in gold-catalyzed reactions. Only gold(III) chloride allowed a conversion of the furandialkynes into the corresponding phenol derivative and a further conversion of the ortho-alkynylfurans into benzofurans. Free hydroxy groups in the substrate led to competing hydroalkoxylations to give acylfurans or benzofuran spiroketals.

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CCDC 631589 (7c), 687063 (7g), 631588 (7h), 631590 (10e) and 687064 (15g) contain the supplementary crystallographic data for this paper. These data can be obtained online free of charge or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk