Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 27, 2019
Previous Article Next Article

Enantioselective photoredox dehalogenative protonation

Author affiliations

Abstract

We report an enantioselective photoredox dehalogenative protonation as a new type of asymmetric protonation. As a paradigm, with a cooperative catalytic system consisting of a chiral H-bonding catalyst and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer that is irradiated with visible light, a range of cyclic and acyclic ketones with labile chiral secondary C–F, C–Cl and C–Br bonds at the α-position were obtained in high yields with good to excellent enantioselectivities (up to >99% ee) by using a secondary amine as the terminal reductant. Given the ready accessibility of halides, the success of this work should provide inspiration for constructing diverse chiral α-tertiary carbonyls and their variants.

Graphical abstract: Enantioselective photoredox dehalogenative protonation

Back to tab navigation

Supplementary files

Article information


Submitted
23 Apr 2019
Accepted
29 May 2019
First published
07 Jun 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 6629-6634
Article type
Edge Article

Enantioselective photoredox dehalogenative protonation

M. Hou, L. Lin, X. Chai, X. Zhao, B. Qiao and Z. Jiang, Chem. Sci., 2019, 10, 6629
DOI: 10.1039/C9SC02000D

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