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July 12, 2005Journal of the American Chemical Society370 citationsOpen Access

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

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ASAnna W. SromekMRMarina RubinaVGVladimir Gevorgyan

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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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Cite This Study

Sromek et al. (2005) studied this question.

synapsesocial.com/papers/6a06fbe85589773960842b70https://doi.org/10.1021/ja053290y
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