Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 26, Pages 10372-10383Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b04111
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- EPFL
- Swiss National Science Foundation [200021_157085]
- Swiss National Science Foundation (SNF) [200021_157085] Funding Source: Swiss National Science Foundation (SNF)
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Densely substituted fused aromatic triazenes can be prepared by [2 + 2 + 2] cyclotrimerization reactions of 1-alkynyl triazenes. The Cp*Ru-catalyzed cyclization proceeds well with both simple alkynyl triazenes and tethered 1-diynyl triazenes. Attractively, the methodology can be extended to pyridine synthesis by replacing an alkyne with a nitrile. The reaction is regioselective and yields the sterically more hindered product. The triazene group precisely installed on the synthesized aryl and pyridyl ring is a highly versatile moiety, which is effortlessly converted into the most important and frequently used functional aryl substituents, including fluorides. It is also suited for intramolecular transformations to afford a variety of valuable heterocycles. The coordination chemistry of alkynyl triazenes and Cp*RuCl was studied and led to the structural characterization of a Cp*RuCl(eta(2)-alkyne) complex, a Cp*RuCl(eta(4)-cyclobutadiene) complex, and an unusual dinuclear Ru complex with a bridging tetramethylfulvene ligand. Complexes of this type are potentially involved in catalyst deactivation pathways.
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