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Communication

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

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Anna W. Sromek, Marina Rubina, and Vladimir Gevorgyan*

Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061

J. Am. Chem. Soc., 2005, 127 (30), pp 10500–10501

DOI: 10.1021/ja053290y

Publication Date (Web): July 12, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, vlad@uic.edu

Abstract

Selective 1,2-iodine, bromine, and chlorine migration in haloallenyl ketones in the presence of Au catalyst has been demonstrated. It was found that, depending on the nature of the Au catalyst used, either selective bromine migration or hydrogen shift occurs, leading to the formation of 3- or 2-bromofurans, respectively. Halirenium intermediate was proposed for the unusual 1,2-halogen migration. This cascade transformation allows for mild and efficient synthesis of various types of 3-halofurans.

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Published In Issue August 03, 2005
Received May 19, 2005

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Communication

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Metal-Catalyzed 1,2-Shift of Diverse Migrating Groups in Allenyl Systems as a New Paradigm toward Densely Functionalized Heterocycles

Mechanistically Diverse Copper-, Silver-, and Gold-Catalyzed Acyloxy and Phosphatyloxy Migrations: Efficient Synthesis of Heterocycles via Cascade Migration/Cycloisomerization Approach

Mechanistic Insights into the Gold-Catalyzed Cycloisomerization of Bromoallenyl Ketones: Ligand-Controlled Regioselectivity

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