1-dimethylphenylsilyl-1-phenyl-2,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene | 1443743-81-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-dimethylphenylsilyl-1-phenyl-2,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene
• 英文别名: Dimethyl-phenyl-[1-phenyl-2,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]silane；dimethyl-phenyl-[1-phenyl-2,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]silane
• CAS: 1443743-81-4
• 化学式: C₂₈H₄₀B₂O₄Si
• 分子量: 490.331
• InChiKey: DDFWKRXCKUNSHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-dimethylphenylsilyl-1-phenyl-2,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三叔丁基膦 、 溴 、 sodium methylate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (E)-1-bromo-1-phenyl-2-(4-trifluoromethylphenyl)-2-(4-methoxyphenyl)ethene
  参考文献：
  名称：

  Selective Synthesis of Multisubstituted Olefins Utilizing gem- and vic-Diborylated Vinylsilanes Prepared by Silylborylation of an Alkynylboronate and Diborylation of Alkynylsilanes

  摘要：

  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.

  DOI：

  10.1021/jo4024057
• 作为产物：
  描述：

  异丙醇频哪醇硼酸酯 在 1,1,3,3-四甲基丁基异腈 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 1-dimethylphenylsilyl-1-phenyl-2,2-bis(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

• Ligand-Dependent-Controlled Copper-Catalyzed Regio- and Stereoselective Silaboration of Alkynes
  作者：Meng Zhao、Cui-Cui Shan、Zi-Lu Wang、Chao Yang、Yao Fu、Yun-He Xu

  DOI：10.1021/acs.orglett.9b02160

  日期：2019.8.2

  A copper-catalyzed highly regio- and stereoselective silaboration of alkynes was developed. In this work, direct cis-difunctionalization of alkynes was realized with silaboronate reagent and copper catalyst in aprotic solvents. The regiodivergent silaborations were controlled by tuning the copper catalysts and phosphine ligands used in reactions. This protocol provides an efficient and practical method

  开发了铜催化的炔烃的高度区域和立体选择性硅烷化。在这项工作中，在非质子传递溶剂中，使用了硅铝硼酸盐试剂和铜催化剂，实现了炔烃的直接顺式双官能化。通过调节反应中所用的铜催化剂和膦配体来控制区域发散性硅烷化。该协议为合成具有特定立体选择性的多取代官能化烯烃提供了一种有效而实用的方法。
• 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.
• Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Silylborylation of an Alkynylboronate/Chemoselective Cross-Coupling Sequences
  作者：Jiao Jiao、Kiyohiko Nakajima、Yasushi Nishihara

  DOI：10.1021/ol401333j

  日期：2013.7.5

  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.