benzyldimethylsilyl trifluoromethanesulfonate | 1612798-07-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: benzyldimethylsilyl trifluoromethanesulfonate
• 英文别名: Benzyldimethylsilyl triflate；[benzyl(dimethyl)silyl] trifluoromethanesulfonate
• CAS: 1612798-07-8
• 化学式: C₁₀H₁₃F₃O₃SSi
• 分子量: 298.358
• InChiKey: YTEYNTJDCQUDMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-叔丁基苯乙烯 、 benzyldimethylsilyl trifluoromethanesulfonate 在 bis(1,5-cyclooctadiene)nickel (0) 、 三乙胺 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以67%的产率得到(E)-benzyl(4-(tert-butyl)styryl)dimethylsilane
  参考文献：
  名称：

  The first example of nickel-catalyzed silyl-Heck reactions: direct activation of silyl triflates without iodide additives

  摘要：

  For the first time, nickel-catalyzed silyl-Heck reactions are reported. Using simple phosphine-supported nickel catalysts, direct activation of silyl triflates has been achieved. These results contrast earlier palladium-catalyzed systems, which require iodide additives to activate silyl-triflates. These nickel-based catalysts exhibit good functional group tolerance in the preparation of vinyl silanes, and unlike earlier systems, allows for the incorporation of trialkylsilanes larger than Me₃Si.

  DOI：

  10.1016/j.tet.2014.03.021

文献信息

• The first example of nickel-catalyzed silyl-Heck reactions: direct activation of silyl triflates without iodide additives
  作者：Jesse R. McAtee、Sara E.S. Martin、Andrew P. Cinderella、William B. Reid、Keywan A. Johnson、Donald A. Watson

  DOI：10.1016/j.tet.2014.03.021

  日期：2014.7

  For the first time, nickel-catalyzed silyl-Heck reactions are reported. Using simple phosphine-supported nickel catalysts, direct activation of silyl triflates has been achieved. These results contrast earlier palladium-catalyzed systems, which require iodide additives to activate silyl-triflates. These nickel-based catalysts exhibit good functional group tolerance in the preparation of vinyl silanes, and unlike earlier systems, allows for the incorporation of trialkylsilanes larger than Me₃Si.