(Z)-trimethyl(2-phenyl-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane | 1512848-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-trimethyl(2-phenyl-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane
• 英文别名: trimethyl-[(Z)-2-phenyl-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]silane
• CAS: 1512848-89-3
• 化学式: C₂₃H₃₈B₂O₄Si
• 分子量: 428.26
• InChiKey: BHQQQXDLIUBVQH-VHEBQXMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-trimethyl(2-phenyl-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) 、 三叔丁基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 生成 (E)-1-(trimethylsilyl)-1-(4-trifluoromethylphenyl)-2-phenyl-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：

  苯乙炔 在 四(三苯基膦)铂 、 乙基溴化镁 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 (Z)-trimethyl(2-phenyl-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane
  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

文献信息

• An experimental and theoretical study into the facile, homogenous (N-heterocyclic carbene)₂-Pd(0) catalyzed diboration of internal and terminal alkynes
  作者：Melvyn B. Ansell、Vitor H. Menezes da Silva、Gabriel Heerdt、Ataualpa A. C. Braga、John Spencer、Oscar Navarro

  DOI：10.1039/c6cy01266c

  日期：——

  diboration of terminal and internal alkynes, yielding a number of novel and known syn-1,2-diborylalkenes in a 100% stereoselective manner. DFT calculations suggest that a similar reaction pathway to that proposed for platinum phosphine analogues is followed, and that destabilization of key intermediates by the NHCs is vital to the overall success for the palladium-catalyzed B–B addition to alkynes.

  Pd（ITMe）2（PhC CPh）在末端炔和内部炔的史无前例的均相催化二硼化反应中充当高反应性的预催化剂，以100％立体选择性的方式产生了许多新颖且已知的syn -1,2-二硼基烯烃。DFT计算表明，遵循了与建议的铂膦类似物相似的反应途径，并且NHC使关键中间体失稳对于钯催化炔烃向B-B加成的整体成功至关重要。
• Solvent- and Ligand-free Diboration of Alkynes and Alkenes Catalyzed by Platinum Nanoparticles on Titania
  作者：Francisco Alonso、Yanina Moglie、Laura Pastor-Pérez、Antonio Sepúlveda-Escribano

  DOI：10.1002/cctc.201300946

  日期：2014.3

  alkynes and alkenes under solvent‐ and ligand‐free conditions in air. The cis‐1,2‐diborylalkenes and 1,2‐diborylalkanes were obtained in moderate to excellent yields following, in most cases, a simple filtration workup protocol. The versatility of the cis‐1,2‐diboronvinyl compounds was demonstrated in a series of organic transformations, including the Suzuki–Miyaura cross coupling and the boron–halogen

  在无溶剂和无配体的条件下，负载在二氧化钛上的铂纳米颗粒可有效催化炔烃和烯烃的缩孔反应。所述顺式中等以下，获得以优异的产率-1,2- diborylalkenes和1,2- diborylalkanes，在大多数情况下，一个简单的过滤后处理的协议。通过一系列有机转化，包括Suzuki-Miyaura交叉偶联和硼-卤素交换，证明了顺式1,2-二硼烷乙烯基化合物的多功能性。
• Hydroboration and Diboration of Internal Alkynes Catalyzed by a Well-Defined Low-Valent Cobalt Catalyst
  作者：Laura Ferrand、Ye Lyu、Alejandro Rivera-Hernández、Brendan Fallon、Muriel Amatore、Corinne Aubert、Marc Petit

  DOI：10.1055/s-0036-1588996

  日期：2017.9

  stereoselective hydroboration of internal alkynes is reported. Extension to the diboration of internal alkynes is also related using the same reaction conditions. The use of a simple well-defined low-valent cobalt(I) catalyst [HCo(PMe3)4] capable of performing the regio- and stereoselective hydroboration of internal alkynes is reported. Extension to the diboration of internal alkynes is also related using the same

  作为有机合成专题钴的一部分出版 抽象 据报道，使用能够进行内部炔的区域和立体选择性硼氢化的简单定义明确的低价钴（I）催化剂[HCo（PMe 3）4 ]。使用相同的反应条件，内部炔烃的扩硼作用也涉及到。 据报道，使用能够进行内部炔的区域和立体选择性硼氢化的简单定义明确的低价钴（I）催化剂[HCo（PMe 3）4 ]。使用相同的反应条件，内部炔烃的扩硼作用也涉及到。
• Sodium-Metal-Promoted Reductive 1,2-<i>syn</i>-Diboration of Alkynes with Reduction-Resistant Trimethoxyborane
  作者：Shiori Ito、Mizuki Fukazawa、Fumiya Takahashi、Keisuke Nogi、Hideki Yorimitsu

  DOI：10.1246/bcsj.20200110

  日期：2020.10.15

  Reductive 1,2-diboration of alkynes has been accomplished by means of sodium dispersion in the presence of trimethoxyborane as a reduction-resistant boron electrophile. Two boron moieties can be introduced onto alkynes with excellent syn selectivity to afford the corresponding (Z)-1,2-diborylalkenes. Bis(borate) species generated in situ can be involved in one-pot Suzuki-Miyaura arylation, formal arylboration of alkynes thus being executed.

  摘要 在三甲氧基硼烷作为抗还原性硼亲电体的存在下，通过钠分散法完成了炔烃的还原性 1,2-二化反应。在炔烃上引入两个硼分子具有极佳的同步选择性，从而得到相应的 (Z)-1,2-二硼酸烯。原位生成的双（硼酸）物种可参与一锅式 Suzukii-Miyaura 芳基化反应，从而实现炔烃的正式芳基硼化。
• 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.