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Categories: Synthesis of O-Heterocycles

Synthesis of 2,5-Dihydrofurans

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Allenylidene-ruthenium complexes on protonation with HOTf are rearranged to indenylidene-ruthenium complexes, which are efficient catalyst precursors for ring-opening metathesis polymerization, ring-closing metathesis and enyne metathesis of a variety of substrates.
R. Castarlenas, C. Vovard, C. Fischmeister, P. H. Dixneuf, J. Am. Chem. Soc., 2006, 128, 4079-4089.


The use of cationic silver (AgSbF4) as a catalyst for intra- and intermolecular alkyne-carbonyl coupling is described.
J. U. Rhee, M. J. Krische, Org. Lett., 2005, 7, 2493-2495.


Conversion of unsaturated ketones and aldehydes derived from the cycloisomerization of primary and secondary propargyl diynols in the presence of [CpRu(CH3CN)3]PF6 to 1-azatrienes and a subsequent electrocyclization-dehydration provides pyridines with excellent regiocontrol.
B. M. Trost, A. C. Gutierrez, Org. Lett., 2007, 9, 1473-1476.


The reduction of various hetero- and carbocyclic aromatic compounds under ammonia free conditions uses LiDBB as a source of electrons, bis(methoxyethyl)amine (BMEA) as a protonating agent, and THF as a solvent. In contrast to Birch type conditions, the described ammonia free conditions allow the use of reactive electrophiles.
T. J. Donohoe, D. House, J. Org. Chem., 2002, 67, 5015-5018.