title: Palladium-catalyzed tandem cyclization/Suzuki coupling of 1,6-enynes: reaction scope and mechanism.
abstract: A palldium(0)-catalyzed tandem cyclization/Suzuki coupling reaction of various 1,6-enyne substrates was developed. This Pd-catalyzed enyne cyclization reaction represents a new process for the synthesis of stereodefined alpha-arylmethylene-gamma-butyrolactones, lactams, multifunctional tetrahydrofurans, pyrrolidines, and cyclopentanes. The mechanism of the reaction was studied by the employment of different enyne isomers and boronic acids; a pi-allyl palladium intermediate was suggested to explain the formation of the cyclic products. The stereochemistry of this reaction can be well explained by a chairlike transition state.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
authors.forename: Gangguo
authors.initials: G
authors.lastname: Zhu
authors.forename: Xiaofeng
authors.initials: X
authors.lastname: Tong
authors.forename: Jiang
authors.initials: J
authors.lastname: Cheng
authors.forename: Yanhui
authors.initials: Y
authors.lastname: Sun
authors.forename: Dao
authors.initials: D
authors.lastname: Li
authors.forename: Zhaoguo
authors.initials: Z
authors.lastname: Zhang
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D000480:Alkynes; D010165:Palladium