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Synthesis of stereo-defined 1,1,4,4-tetrahalo- and 1,1,4,4-mixed-tetrahalo-1,3-butadienes
Authors:Hui-Jun Zhang  Zhiyi Song  Christian Bruneau
Affiliation:a Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
b Institut de Chimie, UMR 6226, CNRS-Université de Rennes 1, Catalyse et Organométalliques, Campus de Beaulieu, 35042 Rennes Cedex, France
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Abstract:Stereo-defined 1,1,4,4-tetrahalo- and 1,1,4,4-mixed-tetrahalo-1,3-butadienes were obtained in excellent yields via desilylation-halogenation of their corresponding 1,4-bis(trimethylsilyl)-1,4-dihalo-1,3-dienes, which could be readily prepared from the zirconocene-mediated high-yield and high-regioselective cyclo-dimerization of 1-trimethylsilyl-1-alkynes followed by halogenation. These poly-functionalized gem-dihalodienes are potentially useful building blocks.
Keywords:1,1,4,4-Tetrahalo-1,3-butadienes   Desilylation-halogenation   gem-Dihaloalkenes   Zirconacyclopentadienes
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