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- Title
Reductive Chlorination and Bromination of Ketones via Trityl Hydrazones.
- Authors
Reyes, Julius R.; Rawal, Viresh H.
- 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.
- Subjects
CHLORINATION; BROMINATION; KETONES; HYDRAZONES; ALKYL bromides; ALKYL chlorides
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 9, p3077
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201510909