Shelf-Stable (<i>E</i>)- and (<i>Z</i>)-Vinyl-λ<sup>3</sup>-chlorane: A Stereospecific Hyper-vinylating Agent
作者:Yuichiro Watanabe、Taisei Takagi、Kazunori Miyamoto、Junichiro Kanazawa、Masanobu Uchiyama
DOI:10.1021/acs.orglett.0c00924
日期:2020.5.1
We report the first stereoselective synthesis of stable (E)- and (Z)-β-chlorovinyl-λ3-chlorane via direct mesitylation of 1,2-dichloroethylene with mesityldiazonium tetrakis(pentafluorophenyl)borate under mild reaction conditions. The structure of the (E)-vinyl-λ3-chlorane was established by single-crystal X-ray analysis. Because of the enormously high leaving group ability of the aryl-λ3-chloranyl
我们报道了在温和的反应条件下,通过 1,2-二氯乙烯与四(五氟苯基)硼酸异三甲苯酯的直接异丙磺酰化反应,首次立体选择性合成稳定的 (E)- 和 (Z)-β-氯乙烯基-λ3-氯烷。(E)-乙烯基-λ3-氯烷的结构通过单晶X射线分析确定。由于芳基-λ3-氯烷基具有极高的离去基团能力,乙烯基-λ3-氯烷不仅会与极弱的亲核试剂如全氟烷磺酸盐、碘苯和芳烃发生SNVσ型反应,还会与苯基铜(I)发生偶联反应。物种。