Nitrogen heteroaromatic cations by [2+2+2] cycloaddition
- 29 September 2010
- journal article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 9 (2) , 450-462
- https://doi.org/10.1039/c0ob00507j
Abstract
A modular approach to the construction of monocationic quaternary N-heteroaromatic frameworks was developed capitalizing on a direct pyridine-type nitrogen quaternization followed by metal-catalyzed [2+2+2] cycloaddition with gaseous acetylene. The flexibility of the route is demonstrated on 12 diverse scaffolds based on pyridinium, quinolinium, thiazolium, benzothiazolium, imidazolium, and pyrimidinium. Electrochemical study revealed a quinolinium redox system with two electrochemically distinct forms that are interconverted by a homogeneous chemical reaction triggered by fast electron transfers (reduction at −0.7 V and oxidation at −0.05 V).Keywords
This publication has 40 references indexed in Scilit:
- Resolution of a configurationally stable [5]helquat: enantiocomposition analysis of a helicene congener by capillary electrophoresisNew Journal of Chemistry, 2010
- Irregular polarographic currents obey Feigenbaum universality route from order to chaosCollection of Czechoslovak Chemical Communications, 2009
- A Photocontrolled Molecular Switch Regulates Paralysis in a Living OrganismJournal of the American Chemical Society, 2009
- The economies of synthesisChemical Society Reviews, 2009
- Bio- and air-tolerant carbon–carbon bond formations via organometallic ruthenium catalysisCollection of Czechoslovak Chemical Communications, 2009
- Amidine Dications: Isolation and [Fe]-Hydrogenase-Related HydrogenationJournal of the American Chemical Society, 2009
- Ring-Closing Metathesis Reactions on Azinium Salts: Straightforward Access to Quinolizinium Cations and Their Dihydro DerivativesThe Journal of Organic Chemistry, 2009
- Enyne ring-closing metathesis on heteroaromatic cationsChemical Communications, 2006
- Ruthenium(II)-Catalyzed Selective Intramolecular [2 + 2 + 2] Alkyne CyclotrimerizationsJournal of the American Chemical Society, 2003
- A Highly Efficient and Flexible Synthesis of Substituted Carbazoles by Rhodium-Catalyzed Inter- and Intramolecular Alkyne CyclotrimerizationsAngewandte Chemie International Edition in English, 2002