Jump to main content
Jump to site search


Reversal of reaction type selectivity by Lewis acid coordination: the ortho photocycloaddition of 1- and 2-naphthaldehyde

Author affiliations

Abstract

The value of a specific substrate class for synthetic applications is greatly enhanced if different types of reactions can be performed selectively upon a judicious choice of reaction conditions. In the present study it was shown that the typical photochemical behaviour of naphthaldehydes is completely altered in the presence of Lewis acids. Without Lewis acids, reactions at the carbonyl group are exclusively observed while Lewis acids facilitate a visible light-mediated cycloaddition at the arene core providing access to products of aromatic C–H functionalization via cyclobutane intermediates.

Graphical abstract: Reversal of reaction type selectivity by Lewis acid coordination: the ortho photocycloaddition of 1- and 2-naphthaldehyde

Back to tab navigation

Supplementary files

Publication details

The article was received on 04 Jul 2019, accepted on 26 Jul 2019 and first published on 29 Jul 2019


Article type: Edge Article
DOI: 10.1039/C9SC03315G
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

  •   Request permissions

    Reversal of reaction type selectivity by Lewis acid coordination: the ortho photocycloaddition of 1- and 2-naphthaldehyde

    S. Stegbauer, N. Jeremias, C. Jandl and T. Bach, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03315G

    This article is licensed under a Creative Commons Attribution-NonCommercial 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 and it is not used for commercial purposes.

    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