Jump to main content
Jump to site search

Issue 19, 2018
Previous Article Next Article

β C–H di-halogenation via iterative hydrogen atom transfer

Author affiliations

Abstract

A radical relay strategy for mono- and di-halogenation (iodination, bromination, and chlorination) of sp3 C–H bonds has been developed. This first example of β C–H di-halogenation is achieved through sequential C–H abstraction by iterative, hydrogen atom transfer (HAT). A double C–H functionalization is enabled by in situ generated imidate radicals, which facilitate selective N˙ to C˙ radical translocation and tunable C–X termination. The versatile, geminal di-iodide products are further elaborated to β ketones and vinyl iodides. Mechanistic experiments explain the unique di-functionalization selectivity of this iterative HAT pathway, wherein the second C–H iodination is twice as fast as the first.

Graphical abstract: β C–H di-halogenation via iterative hydrogen atom transfer

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Mar 2018, accepted on 19 Apr 2018 and first published on 30 Apr 2018


Article type: Edge Article
DOI: 10.1039/C8SC01214H
Chem. Sci., 2018,9, 4500-4504
  • Open access: Creative Commons BY license
  •   Request permissions

    β C–H di-halogenation via iterative hydrogen atom transfer

    E. A. Wappes, A. Vanitcha and D. A. Nagib, Chem. Sci., 2018, 9, 4500
    DOI: 10.1039/C8SC01214H

    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.

Search articles by author

Spotlight

Advertisements