Crossed McMurry coupling reactions for porphycenic macrocycles: Non-statistical selectivity and rationalisation

Thomas Y. Cowie, Lorna Kennedy, Justyna M. Zurek, Martin J. Paterson, Magnus W P Bebbington

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3 Citations (Scopus)
244 Downloads (Pure)

Abstract

Crossed McMurry reactions of bifuran- or bithiophenedicarbaldehydes with bipyrroledicarbaldehydes have been studied for the first time. Only those porphycenic macrocycles derived from homocoupled McMurry products were formed. The results are explained by using both density functional theory and electron propagator computations to model the electron affinity of the dialdehyde starting materials. It was predicted that bifuran\bithiophene cross-coupling would indeed occur, and this was demonstrated by the first synthesis of a novel dioxa,dithio hetero-porphycenoid annulene. This approach will allow the prior identification of viable substrates for related crossed McMurry reactions.

Original languageEnglish
Pages (from-to)3818-3823
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number17
Early online date29 Apr 2015
DOIs
Publication statusPublished - 2015

Keywords

  • Heterocyclic chemistry
  • Macrocycles
  • McMurry coupling
  • Photochemistry
  • Porphycenes
  • Redox chemistry

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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    Crossed McMurry coupling reactions for porphycenic macrocycles

    Bebbington, M. W. P. (Creator), Heriot-Watt University, 9 Jul 2015

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