4.6 Article

Iron-catalysed asymmetric carboazidation of styrenes

Journal

NATURE CATALYSIS
Volume 4, Issue 1, Pages 28-35

Publisher

NATURE RESEARCH
DOI: 10.1038/s41929-020-00551-4

Keywords

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Funding

  1. National Key R&D Programme of China [2017YFA0700103]
  2. NSFC [21672213, 21871258, 21922112]
  3. Strategic Priority Research Programme of the Chinese Academy of Sciences [XDB20000000]
  4. Haixi Institute of CAS [CXZX-2017-P01]
  5. Innovative Research Teams Programme II of Fujian Normal University in China [IRTL1703]
  6. Shenzhen STIC [JCYJ20170412150343516]
  7. Shenzhen San-Ming Project [SZSM201809085]

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The study reports a radical asymmetric carboazidation of olefins via an iron-catalysed group transfer mechanism, providing valuable chiral halogenated organoazides from inexpensive industrial chemical feedstocks. The method is supported by mechanistic studies and is expected to inspire further development of enantioselective radical reactions.
Carboazidation of olefins is an efficient process to convert hydrocarbons directly into nitrogen-containing molecules. Such chemicals find broad applications in medicine and material sciences. Despite the fast development of carboazidation reactions, asymmetric radical carboazidations are still elusive. Here, we report a radical asymmetric carboazidation of olefins via an iron-catalysed group transfer mechanism. The method affords valuable chiral halogenated organoazides from inexpensive industrial chemical feedstocks. This radical azidation reaction is supported by mechanistic studies and should inspire further development of enantioselective radical reactions.

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