Jump to main content
Jump to site search


C–H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

Author affiliations

Abstract

The difficulty in accessing and safely utilising non-stabilised diazo species has in the past limited the application of this class of compounds. Here we explore further the use of oxadiazolines, non-stabilised diazo precursors which are bench stable, in direct, non-catalytic, aldehyde C–H functionalisation reactions under UV photolysis in flow and free from additives. Commercially available aldehydes are coupled to afford unsymmetrical aryl–alkyl and alkyl–alkyl ketones while mild conditions and lack of transition metal catalysts allow for exceptional functional group tolerance. Examples are given on small scale and in a larger scale continuous production.

Graphical abstract: C–H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

Back to tab navigation

Supplementary files

Publication details

The article was received on 30 Jul 2018, accepted on 20 Aug 2018 and first published on 11 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC06202A
Citation: Chem. Commun., 2018, Advance Article
  • Open access: Creative Commons BY license
  •   Request permissions

    C–H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

    P. Dingwall, A. Greb, L. N. S. Crespin, R. Labes, B. Musio, J. Poh, P. Pasau, D. C. Blakemore and S. V. Ley, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC06202A

    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