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Densely substituted fused aromatic triazenes can be prepared by [2 + 2 + 2] cyclotrimerization reactions of 1-alkynyl triazenes. The CpRu-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 CpRuCl was studied and led to the structural characterization of a CpRuCl(η2-alkyne) complex, a CpRuCl(η4-cyclobutadiene) complex, and an unusual dinuclear Ru complex with a bridging tetramethylfulvene ligand. Complexes of this type are potentially involved in catalyst deactivation pathways.
Moreno Lelli, Pierrick Berruyer, David Benjamin Roger Antoine Gajan, Zhuoran Wang
Rosario Scopelliti, Kay Severin, Farzaneh Fadaei Tirani, Bastiaan Kooij, Zhaowen Dong
Rosario Scopelliti, Kay Severin, Farzaneh Fadaei Tirani, Paul Varava, Wolfram Feuerstein