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.
|Journal||European Journal of Organic Chemistry|
|Early online date||29 Apr 2015|
|Publication status||Published - 2015|
- Heterocyclic chemistry
- McMurry coupling
- 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