Abstract
The use of hydrazine-catalyzed ring-closing carbonyl–olefin metathesis (RCCOM) to synthesize polycyclic heteroaromatic (PHA) compounds is described. In particular, substrates bearing Lewis basic functionalities such as pyridine rings and amines, which strongly inhibit acid catalyzed RCCOM reactions, are shown to be compatible with this reaction. Using 5 mol% catalyst loadings, a variety of PHA structures can be synthesized from biaryl alkenyl aldehydes, which themselves are readily prepared by cross-coupling.
Highlights
All publication charges for this article have been paid for by the Royal Society of Chemistry
Using 5 mol% catalyst loadings, a variety of polycyclic heteroaromatic (PHA) structures can be synthesized from biaryl alkenyl aldehydes, which themselves are readily prepared by cross-coupling
One potentially advantageous strategy for PHA synthesis is the use of ring-closing carbonyl–ole n metathesis[15] (RCCOM) to forge one of the PHA rings, starting from a suitably disposed alkenyl aldehyde precursor 2 that can be assembled by cross-coupling (Fig. 1B)
Summary
All publication charges for this article have been paid for by the Royal Society of Chemistry. The use of hydrazine-catalyzed ring-closing carbonyl–olefin metathesis (RCCOM) to synthesize polycyclic heteroaromatic (PHA) compounds is described. Substrates bearing Lewis basic functionalities such as pyridine rings and amines, which strongly inhibit acid catalyzed RCCOM reactions, are shown to be compatible with this reaction.
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