title: Nickel-catalyzed formation of cyclopentenone derivatives via the unique cycloaddition of α,β-unsaturated phenyl esters with alkynes.
abstract: Oxygen-containing organic compounds, such as ethers, carboxylates, and carbamates, have recently received increasing attention because of their newly discovered applications as electrophiles in cross-coupling reactions via transition metal-catalyzed C-O bond activation. However, no cycloaddition reaction involving their C-O bond activation has been demonstrated thus far. The present study developed a Ni(0)-catalyzed unique [3+2] cycloaddition reaction of α,β-unsaturated phenyl esters with alkynes in (i)PrOH to yield cyclopentenone derivatives.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, Japan. ohashi@chem.eng.osaka-u.ac.jp
authors.forename: Masato
authors.initials: M
authors.lastname: Ohashi
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Taniguchi
authors.forename: Sensuke
authors.initials: S
authors.lastname: Ogoshi
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D003517:Cyclopentanes; D004952:Esters; D009942:Organometallic Compounds; D009532:Nickel; C013905:cyclopentenone