(E)-1-(dimethylphenylsilyl)-1-phenyl-2-(4-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene | 1443743-95-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-(dimethylphenylsilyl)-1-phenyl-2-(4-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene
• CAS: 1443743-95-0
• 化学式: C₂₈H₃₂BClO₂Si
• 分子量: 474.91
• InChiKey: OJWUJTOEDCPYQI-QPLCGJKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (二甲基苯硅烷基)硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 1,1,3,3-四甲基丁基异腈 、 palladium diacetate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 14.0h， 生成 (Z)-1-(dimethylphenylsilyl)-1-phenyl-2-(4-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene 、 (E)-1-(dimethylphenylsilyl)-1-phenyl-2-(4-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene
  参考文献：
  名称：

  Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Silylborylation of an Alkynylboronate/Chemoselective Cross-Coupling Sequences

  摘要：

  A highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe2Si-B-pin undergoes a Pd(OAc)(2)/(t)OctNC-catalyzed syn-addition to the alkynylboronate to yield 1-phenyl-1-silyl-2,2-diborylethene with high regioselectivity. The product 1-phenyl-1-silyl-2,2-diborylethene is then chemoselectively arylated by Suzuki-Miyaura coupling to afford (2)-1-silyl-2-borylstilbene derivatives. This approach is extended to the synthesis of a tetraarylated olefin with four different substituents.

  DOI：

  10.1021/ol401333j

文献信息

• Selective Synthesis of Multisubstituted Olefins Utilizing <i>gem</i>- and <i>vic</i>-Diborylated Vinylsilanes Prepared by Silylborylation of an Alkynylboronate and Diborylation of Alkynylsilanes
  作者：Jiao Jiao、Keita Hyodo、Hao Hu、Kiyohiko Nakajima、Yasushi Nishihara

  DOI：10.1021/jo4024057

  日期：2014.1.3

  The synthesis of a series of gem- and vic-diborylated vinylsilanes was accomplished via highly selective transition-metal-catalyzed syn-dimetalation to the alkynylmetal species. This protocol served as a general synthetic method toward regio- and stereodefined multisubstituted olefins. The key steps are the diastereoselective Suzuki-Miyaura cross-coupling reactions of gem- and vic-diborylated vinylsilanes, in which the two boron groups showed discrete reactivities to afford diverse precursors of multisubstituted olefins.