Potassium (2-bromo-2-phenylvinyl)trifluoroborate | 219718-89-5

• 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: Potassium (2-bromo-2-phenylvinyl)trifluoroborate
• 英文别名: potassium;[(Z)-2-bromo-2-phenylethenyl]-trifluoroboranuide
• CAS: 219718-89-5
• 化学式: C₈H₆BBrF₃*K
• 分子量: 288.944
• InChiKey: KSODWGWQNMCMLU-PHZXCRFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险类别：
  8
• 危险性防范说明：
  P501,P260,P234,P264,P280,P390,P303+P361+P353,P301+P330+P331,P363,P304+P340+P310,P305+P351+P338+P310,P406,P405
• 危险品运输编号：
  3261
• 危险性描述：
  H314,H290
• 包装等级：
  III

反应信息

• 作为反应物：
  描述：

  Potassium (2-bromo-2-phenylvinyl)trifluoroborate 在 tetra-N-butylammonium tribromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 以78%的产率得到反式-1,2-二溴-1-苯基-1-丙烯
  参考文献：
  名称：

  Chemoselective Bromodeboronation of Organotrifluoroborates Using Tetrabutylammonium Tribromide: Application in (Z)-Dibromoalkene Syntheses

  摘要：

  Tetrabutylammonium tribromide (TBATB) has been found to be a unique bromodeboronation reagent for organotrifluoroborates. When compared to previously reported bromodeboronation methods, the mild and metal-free reaction conditions tolerate a wider range of functional groups. High regio- and chemoselectivity are observed in the presence of both unsaturated carbon-carbon bonds and aldehyde functional groups. An efficient synthetic route to (Z)-dibromoalkenes from terminal alkynes has been developed using the TBATB-mediated bromodeboronation as a key step.

  DOI：

  10.1021/ol9027144
• 作为产物：
  描述：

  (Z)-2-bromo-2-phenylvinylboronic acid 在 二氟化氢钾 作用下， 以 甲醇 、 水 为溶剂， 生成 Potassium (2-bromo-2-phenylvinyl)trifluoroborate
  参考文献：
  名称：

  Rh(i)-catalyzed formal [2+2+2] cycloadditions of 1,6-diynes with potassium (Z)-(2-bromovinyl)trifluoroborate: a new strategy and a facile entry to polysubstituented benzene derivatives

  摘要：

  以 (Z)-(2-bromovinyl)trifluoroborate 钾作为第三个双原子单元，实现了 Rh(I)- 催化 1,6- 二炔的 [2+2+2] 环加成反应的新策略，为多取代基苯衍生物提供了简便的入口。

  DOI：

  10.1039/c001830a

文献信息

• Facile Preparation of Fluorine-containing Alkenes, Amides and Alcohols <i>via</i> the Electrophilic Fluorination of Alkenyl Boronic Acids and Trifluoroborates
  作者：Nicos Petasis、Andrei Yudin、Ilia Zavialov、G. Prakash、George Olah

  DOI：10.1055/s-1997-3228

  日期：1997.5

  Reaction of alkenyl boronic acids, or preferably alkenyl trifluoroborates, with one equivalent of SelectfluorTM gives the corresponding alkenyl fluorides. A similar reaction with two equivalents of SelectfluorTM in water or a nitrile solvent gives difluoromethyl-substituted alcohols and amides respectively.

  烯基硼酸（或更优选的烯基三氟硼酸盐）与一当量的Selectfluor™反应，生成相应的烯基氟化物。与两当量的Selectfluor™在水或氰类溶剂中进行类似反应，分别生成二氟甲基取代的醇和酰胺。
• Chemoselective Bromodeboronation of Organotrifluoroborates Using Tetrabutylammonium Tribromide: Application in (<i>Z</i>)-Dibromoalkene Syntheses
  作者：Min-Liang Yao、Marepally Srinivasa Reddy、Li Yong、Ingrid Walfish、David W. Blevins、George W. Kabalka

  DOI：10.1021/ol9027144

  日期：2010.2.19

  Tetrabutylammonium tribromide (TBATB) has been found to be a unique bromodeboronation reagent for organotrifluoroborates. When compared to previously reported bromodeboronation methods, the mild and metal-free reaction conditions tolerate a wider range of functional groups. High regio- and chemoselectivity are observed in the presence of both unsaturated carbon-carbon bonds and aldehyde functional groups. An efficient synthetic route to (Z)-dibromoalkenes from terminal alkynes has been developed using the TBATB-mediated bromodeboronation as a key step.
• Rh(i)-catalyzed formal [2+2+2] cycloadditions of 1,6-diynes with potassium (Z)-(2-bromovinyl)trifluoroborate: a new strategy and a facile entry to polysubstituented benzene derivatives
  作者：Xianjie Fang、Junyao Sun、Xiaofeng Tong

  DOI：10.1039/c001830a

  日期：——

  A new strategy for Rh(I)-catalyzed [2+2+2] cycloadditions of 1,6-diynes with potassium (Z)-(2-bromovinyl)trifluoroborate as the third two-atom unit has been realized, which provides a facile entry to polysubstituented benzene derivatives.

  以 (Z)-(2-bromovinyl)trifluoroborate 钾作为第三个双原子单元，实现了 Rh(I)- 催化 1,6- 二炔的 [2+2+2] 环加成反应的新策略，为多取代基苯衍生物提供了简便的入口。