Jump to main content
Jump to site search


Intermolecular radical carboamination of alkenes

Author affiliations

Abstract

Vicinal alkene carboamination is a highly efficient and practical synthetic strategy for the straightforward preparation of diverse and valuable amine derivatives starting from simple compounds. During the last decade that approach has found continuous research interests and various practical methods have been developed using transition-metal catalysis. Driven by the renaissance of synthetic radical chemistry, intermolecular radical alkene carboamination comprising a C–C bond and a C–N bond forming step has been intensively investigated recently culminating in novel strategies and improved protocols which complement existing methodologies. Radical alkene carboamination can be achieved via three different reaction modes. Such cascades can proceed through N-radical addition to an alkene with subsequent C–C bond formation leading to 2,1-carboamination products. Alternatively, the C–C bond can be installed prior to the C–N bond via initial C-radical addition to the alkene with subsequent β-amination resulting in 1,2-carboamination. The third mode comprises initial single electron oxidation of the alkene to the corresponding alkene radical cation that gets trapped by an N-nucleophile and the cascade is terminated by radical C–C bond formation. In this review, the three different conceptual approaches will be discussed and examples from the recent literature will be presented. Further, the reader will get insights into the mechanism of the different transformations.

Graphical abstract: Intermolecular radical carboamination of alkenes

Back to tab navigation

Article information


Submitted
18 Nov 2019
First published
14 Feb 2020

This article is Open Access

Chem. Soc. Rev., 2020, Advance Article
Article type
Review Article

Intermolecular radical carboamination of alkenes

H. Jiang and A. Studer, Chem. Soc. Rev., 2020, Advance Article , DOI: 10.1039/C9CS00692C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements