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1,2-Halogen Migration in Haloallenyl Ketones: Regiodivergent Synthesis of Halofurans

Anna W. Sromek, Marina Rubina and Vladimir Gevorgyan*

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, Email: vladuic.edu

A. W. Sromek, M. Rubina, V. Gevorgyan, J. Am. Chem. Soc., 2005, 127, 10500-10501.

DOI: 10.1021/ja053290y (free Supporting Information)


Abstract

Different gold catalysts effect either selective bromine migration or hydrogen shift in haloallenyl ketones, leading to the formation of 3- or 2-bromofurans, respectively. AuCl3-catalyzed transformations include 1,2-halogen migrations via proposed halirenium intermediates and allow for mild and efficient synthesis of various types of 3-halofurans.

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Key Words

Furans


ID: J48-Y2005-2520