Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 9, Pages 3077-3080Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510909
Keywords
diastereoselectivity; halogenation; hydrazones; radical reactions; synthetic methods
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Funding
- National Cancer Institute of the NIH [R01 CA101438]
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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 -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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