Jump to main content
Jump to site search


Combining the catalytic enantioselective reaction of visible-light-generated radicals with a by-product utilization system

Author affiliations

Abstract

We report an unusual reaction design in which a chiral bis-cyclometalated rhodium(III) complex enables the stereocontrolled chemistry of photo-generated carbon-centered radicals and at the same time catalyzes an enantioselective sulfonyl radical addition to an alkene. Specifically, employing inexpensive and readily available Hantzsch esters as the photoredox mediator, Rh-coordinated prochiral radicals generated by a selective photoinduced single electron reduction are trapped by allyl sulfones in a highly stereocontrolled fashion, providing radical allylation products with up to 97% ee. The hereby formed fragmented sulfonyl radicals are utilized via an enantioselective radical addition to form chiral sulfones, which minimizes waste generation.

Graphical abstract: Combining the catalytic enantioselective reaction of visible-light-generated radicals with a by-product utilization system

Back to tab navigation

Supplementary files

Publication details

The article was received on 12 Jun 2017, accepted on 16 Aug 2017 and first published on 01 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC02621H
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
  •   Request permissions

    Combining the catalytic enantioselective reaction of visible-light-generated radicals with a by-product utilization system

    X. Huang, S. Luo, O. Burghaus, R. D. Webster, K. Harms and E. Meggers, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC02621H

    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