Polycyclic heteroaromatics <i>via</i> hydrazine-catalyzed ring-closing carbonyl–olefin metathesis
Eun Kee Cho, Phong K. Quach, Yunfei Zhang, Jae Hun Sim, Tristan H. Lambert
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.
Topics & Concepts
Olefin metathesisRing-closing metathesisHydrazine (antidepressant)Ring (chemistry)ChemistryCatalysisClosing (real estate)Olefin fiberCombinatorial chemistryOrganic chemistryMetathesisBusinessChromatographyPolymerPolymerizationFinanceSynthetic Organic Chemistry MethodsChemical Synthesis and AnalysisAsymmetric Synthesis and Catalysis