title: α-Allenyl Ethers as Starting Materials for Palladium Catalyzed Suzuki-Miyaura Couplings of Allenylphosphine Oxides with Arylboronic Acids.
abstract: We disclose here the first palladium-catalyzed Suzuki-Miyaura couplings of aryl ethers functionalized allenylphosphine oxides with arylboronic acids. This new methodology with α-allenyl ethers as starting materials provides a novel approach to generate phosphinoyl 1,3-butadienes and derivatives with medium to excellent yields. The reaction tolerates a variety of functional groups to afford ranges of structurally diverse substituted phosphionyl 1,3-butadienes. For unsymmetrical allene substrates, high stereospecific additions to give E-isomers are usually observed. On the basis of the known palladium and allene chemistry, a mechanism is proposed.
authors.affiliation: †Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
authors.forename: Yao-Zhong
authors.initials: YZ
authors.lastname: Chen
authors.affiliation: †Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
authors.forename: Ling
authors.initials: L
authors.lastname: Zhang
authors.affiliation: †Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
authors.forename: Ai-Min
authors.initials: AM
authors.lastname: Lu
authors.affiliation: †Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
authors.forename: Fang
authors.initials: F
authors.lastname: Yang
authors.affiliation: †Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.|‡CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Wu
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002070:Butadienes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D002070:Butadienes; D004987:Ethers; D009942:Organometallic Compounds; D010087:Oxides; D010720:Phosphines; D010165:Palladium; C031763:1,3-butadiene