Application of 32993-05-8. Let’s face it, organic chemistry can seem difficult to learn. Especially from a beginner’s point of view. Like 32993-05-8, Name is Chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II). In a document type is Article, introducing its new discovery.
Cyclization of the ether enyne 1 catalyzed by [Ru]NCCH3+ ([Ru] = Cp(PPh3)2Ru) in CHCl3 generates a diastereomeric mixture of the substituted tetrahydropyran 11. Presumably, formation of an allenylidene complex is followed by a cyclization by nucleophilic addition of the olefinic group to C? of the ligand giving a boat-like six-membered ring. The diastereoselectivity is controlled by the 1,3-diaxial interaction. The vinylidene complex 7, a precursor of 11, is obtained from 1 and [Ru]Cl. In a mixture of MeOH/CHCl3, the domino cyclization of 1 further affords 14a, a chromene product catalytically. The second cyclization proceeds via nucleophilic addition of the resulting olefinic unit to Calpha of 7. But the ether enyne 3 with a cyclopentyl ring on the olefinic unit undergoes only single cyclization due to steric effect. The propargyl alcohol and the two terminal methyl groups on the olefinic unit shape the cyclization. Thus, similar all-carbon 1,n-enynes (n = 7, 8, 9) 4-6 each with an aromatic linker undergo direct domino cyclization catalyzed by [Ru]NCCH3+, to give derivatives of tricyclic fluorene, phenanthrene and dibenzo[7]annulene, respectively, with no intermediate observed.
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Reference：
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI