lithium pentafluorophenyltrimethoxyborate

• 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: lithium pentafluorophenyltrimethoxyborate
• 英文别名: Li[C6HF5B(OMe)3]；Lithium;trimethoxy-(2,3,4,5,6-pentafluorophenyl)boranuide
• 化学式: C₉H₉BF₅O₃*Li
• 分子量: 277.913
• InChiKey: LWRCLQIGEYLNSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.53
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  对氟碘苯 、 lithium pentafluorophenyltrimethoxyborate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以60%的产率得到2,3,4,4',5,6-hexafluorobiphenyl
  参考文献：
  名称：

  The palladium-catalysed cross-coupling reaction of lithium polyfluorophenyltrimethoxyborates with 4-fluoroiodobenzene

  摘要：

  Li[C6F5B(OMe)(3)]. Li[C6HF4B(OMe)(3)] (all three isomers) and Li[3,4,5-C6H2F3B(OMe)(3)] are the first examples of polyfluorophenyltrimethoxyborate salts which have been applied as reagents to Pd-catalysed cross-coupling reactions. A series of polyfluorinated biphenyls C6H5-nFn-C6H4F-4' were obtained from Li[C6H5-nFnB(OMe)(3)] and the model substrate 4-FC6H4I in the presence of Pd catalysts. The influence of the number and the position of fluorine atoms in the polyfluorophenyltrimetboxyborate salts on the reactivity in the coupling reaction was elucidated. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00088-5
• 作为产物：
  描述：

  硼酸三甲酯 、 五氟苯 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 正戊烷 为溶剂， 反应 2.5h， 以75%的产率得到lithium pentafluorophenyltrimethoxyborate
  参考文献：
  名称：

  The palladium-catalysed cross-coupling reaction of lithium polyfluorophenyltrimethoxyborates with 4-fluoroiodobenzene

  摘要：

  Li[C6F5B(OMe)(3)]. Li[C6HF4B(OMe)(3)] (all three isomers) and Li[3,4,5-C6H2F3B(OMe)(3)] are the first examples of polyfluorophenyltrimethoxyborate salts which have been applied as reagents to Pd-catalysed cross-coupling reactions. A series of polyfluorinated biphenyls C6H5-nFn-C6H4F-4' were obtained from Li[C6H5-nFnB(OMe)(3)] and the model substrate 4-FC6H4I in the presence of Pd catalysts. The influence of the number and the position of fluorine atoms in the polyfluorophenyltrimetboxyborate salts on the reactivity in the coupling reaction was elucidated. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00088-5

文献信息

• Polyfluoroorganoboron-Oxygen Compounds. 7. Studies of Conversion of [(C6HnF5-n)B(OMe)3]- Into [(C6HnF5-n)2B(OMe)2]- (n = 0, 1)
  作者：Nicolai Yu. Adonin、Vadim V. Bardin、Hermann-Josef Frohn

  DOI：10.1135/cccc20081681

  日期：——

  Conversion of salts Li[(C₆H_nF_5-n)B(OMe)₃] (n = 0, 1) into (Li·DME)[(C₆H_nF_5-n)₂B(OMe)₂] was studied in dichloromethane-DME solution. The observed rate constants k decrease from (21.4 ± 0.9) × 10^-3 l mol^-1 s^-1 (Li[C₆F₅B(OMe)₃]) over (6.99 ± 0.11) × 10^-3 l mol^-1 s^-1 (Li[(2,3,5,6-C₆HF₄)B(OMe)₃]) to (2.94 ± 0.05) × 10^-3 l mol^-1 s^-1 (Li[(2,3,4,6-C₆HF₄)B(OMe)₃]), while Li[(2,3,4,5-C₆HF₄)B(OMe)₃] does not undergo any transformation. Hydrolysis of (Li·DME)[(C₆H_nF_5-n)₂B(OMe)₂] leads to corresponding borinic acids, whereas treatment of them with aqueous solution of M[HF₂] (M = Bu₄N, K) acidified with HF results in M[(C₆H_nF_5-n)₂BF₂] in high yields.

  在二氯甲烷-DME溶液中研究了盐Li[(C6HnF5-n)B(OMe)3] (n = 0, 1) 转化为(Li·DME)[(C6HnF5-n)2B(OMe)2]。观察到的速率常数k从(21.4 ± 0.9) × 10-3升摩尔-1秒-1 (Li[C6F5B(OMe)3]) 下降到(6.99 ± 0.11) × 10-3升摩尔-1秒-1 (Li[(2,3,5,6-C6HF4)B(OMe)3])，最终到(2.94 ± 0.05) × 10-3升摩尔-1秒-1 (Li[(2,3,4,6- )B(OMe)3])，而Li[(2,3,4,5- )B(OMe)3] 不发生任何转化。对(Li·DME)[(C6HnF5-n)2B(OMe)2]的水解导致相应的硼酸，而用含HF的水溶液处理它们，结果是高产率的M[(C6HnF5-n)2BF2] (M = Bu4N, K)。