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. 2005 Aug 3;127(30):10500-1.
doi: 10.1021/ja053290y.

1,2-Halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans

Anna W Sromek  1 , Marina Rubina, Vladimir Gevorgyan
Affiliations

1,2-Halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans

Anna W Sromek et al. J Am Chem Soc. .

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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Figures

Scheme 1
Scheme 1. Proposed Pathways for the Synthesis of Halofurans 2 and 3
See this image and copyright information in PMC

References

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