(E)-(4-chlorostyryl)(phenyl)iodonium trifluoromethanesulfonate | 1380240-01-6

• 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: (E)-(4-chlorostyryl)(phenyl)iodonium trifluoromethanesulfonate
• 英文别名: phenyl[(1E)-2-(4-chloro)phenylethenyl]iodonium triflate；[(E)-2-(4-chlorophenyl)ethenyl]-phenyliodanium;trifluoromethanesulfonate
• CAS: 1380240-01-6
• 化学式: CF₃O₃S*C₁₄H₁₁ClI
• 分子量: 490.669
• InChiKey: VBPSKNPVZGNPOE-ASTDGNLGSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  正辛醛 、 (E)-(4-chlorostyryl)(phenyl)iodonium trifluoromethanesulfonate 在 (2R,5R)-2-tert-butyl-3-methyl-5-phenyl-4-imidazolidinone trifluoroacetic acid salt 、 sodium carbonate 、 copper(I) bromide 作用下， 以 乙醚 为溶剂， 生成 (2S)-2-[(E)-2-(4-chlorophenyl)ethenyl]octanal
  参考文献：
  名称：

  Enantioselective α-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis

  摘要：

  The enantioselective alpha-vinylation of aldehydes using vinyl iodonium triflate salts has been accomplished via the synergistic combination of copper and chiral amine catalysis. These mild catalytic conditions provide a direct route for the enantioselective construction of enolizable alpha-formyl vinylic stereocenters without racemization or olefin transposition. These high-value coupling adducts are readily converted into a variety of useful olefin synthons.

  DOI：

  10.1021/ja303116v
• 作为产物：
  描述：

  碘苯二乙酸 、 三氟甲磺酸钠 、 反式-2-(4-氯苯)乙烯硼酸 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.25h， 以65%的产率得到(E)-(4-chlorostyryl)(phenyl)iodonium trifluoromethanesulfonate
  参考文献：
  名称：

  Enantioselective α-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis

  摘要：

  The enantioselective alpha-vinylation of aldehydes using vinyl iodonium triflate salts has been accomplished via the synergistic combination of copper and chiral amine catalysis. These mild catalytic conditions provide a direct route for the enantioselective construction of enolizable alpha-formyl vinylic stereocenters without racemization or olefin transposition. These high-value coupling adducts are readily converted into a variety of useful olefin synthons.

  DOI：

  10.1021/ja303116v

文献信息

• Well-Defined, Shelf-Stable (NHC)Ag(CF₂H) Complexes for Difluoromethylation
  作者：Yang Gu、Dalu Chang、Xuebing Leng、Yucheng Gu、Qilong Shen

  DOI：10.1021/acs.organomet.5b00350

  日期：2015.6.22

  The preparation of the thermally stable, well-defined NHC-ligated difluoromethylated silver complexes la,b is described. The complexes were fully characterized, and the structural assignments were ambiguously further confirmed by single-crystal X-ray diffraction. Reactions of [(SIPr)Ag(CF2H)] with a variety of activated electrophiles such as diaryliodonium salts, vinyl(aryl)iodonium salts, aryldiazonium salts, and acid chlorides in the presence or absence of CuI occurred smoothly at room temperature to generate difluoromethylated compounds in good to excellent yields.