Reductive Chlorination and Bromination of Ketones via Trityl Hydrazones |
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Authors: | Julius R. Reyes Prof. Dr. Viresh H. Rawal |
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Affiliation: | Department of Chemistry, The University of Chicago, Chicago, IL, USA |
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Abstract: | A method is presented for the direct transformation of a ketone to the corresponding reduced alkyl chloride or bromide. The process involves the reaction of a ketone trityl hydrazone with tBuOCl to give a diazene which readily collapses to the α‐chlorocarbinyl radical, reduction of which by a hydrogen atom source gives the alkyl chloride product. The use of N‐bromosuccinimide provides the corresponding alkyl bromide. This unique transformation provides a reductive halogenation that complements Barton's redox‐neutral vinyl halide synthesis. |
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Keywords: | diastereoselectivity halogenation hydrazones radical reactions synthetic methods |
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