potassium 4-cyanophenethyltrifluoroborate | 1086975-14-5

• 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 4-cyanophenethyltrifluoroborate
• CAS: 1086975-14-5
• 化学式: C₉H₈BF₃N*K
• 分子量: 237.074
• InChiKey: CVYBDVJMOLXZGF-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  potassium 4-cyanophenethyltrifluoroborate 在 2,2'-联吡啶 、 三甲基氯硅烷 、 copper(II) choride dihydrate 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 14.0h， 生成 methyl 4-(2-((trifluoromethyl)sulfanyl)ethyl)benzonitrile
  参考文献：
  名称：

  铜催化的伯和仲烷基硼酸的三氟甲基硫醇化

  摘要：

  描述了用亲电子的三氟甲基硫醇化试剂的Cu催化的伯烷基硼酸和仲烷基硼酸的三氟甲基硫醇化。观察到对各种官能团的耐受性。

  DOI：

  10.1021/ol502132j
• 作为产物：
  描述：

  4-氰基苯乙烯 在 (1,3-dimesitylimidazolidin-2-yl)copper(I) chloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.17h， 生成 potassium 4-cyanophenethyltrifluoroborate
  参考文献：
  名称：

  铜催化的伯和仲烷基硼酸的三氟甲基硫醇化

  摘要：

  描述了用亲电子的三氟甲基硫醇化试剂的Cu催化的伯烷基硼酸和仲烷基硼酸的三氟甲基硫醇化。观察到对各种官能团的耐受性。

  DOI：

  10.1021/ol502132j

文献信息

• Orthogonal Reactivity in Boryl-Substituted Organotrifluoroborates
  作者：Gary A. Molander、Deidre L. Sandrock

  DOI：10.1021/ja807076d

  日期：2008.11.26

  A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.
• Utilization of Potassium Vinyltrifluoroborate in the Development of a 1,2-Dianion Equivalent
  作者：Gary A. Molander、Deidre L. Sandrock

  DOI：10.1021/ol900822j

  日期：2009.6.4

  Previous studies of orthogonally reactive dibora species led to the discovery of a unique reactivity pattern associated with potassium vinyltrifluoroborate. Upon hydroboration, the vinyltrifluoroborate generates a 1,2-diboraethane, which is distinct from the 1,1-dibora intermediates generated when traditional alkenyldialkylboron species undergo hydroboration. The 1,2-dianion equivalent thus generated can be envisioned as a building block for the linkage of two different electrophiles via palladium-catalyzed Suzuki-Miyaura cross-couplings.