bis(4-fluorophenyl)iodonium hexafluorophosphate | 91290-89-0

• 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: bis(4-fluorophenyl)iodonium hexafluorophosphate
• 英文别名: Bis(4-fluorophenyl)iodanium;hexafluorophosphate
• CAS: 91290-89-0
• 化学式: C₁₂H₈F₂I*F₆P
• 分子量: 462.061
• InChiKey: KEHJDOXRRLWINF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• 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：
  9

反应信息

• 作为反应物：
  描述：

  2-甲基异喹啉-1(2H)-酮 、 bis(4-fluorophenyl)iodonium hexafluorophosphate 在 silver hexafluoroantimonate 、 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以90%的产率得到8-(4-fluorophenyl)-2-methylisoquinolin-1(2H)-one
  参考文献：
  名称：

  Catalyst Controlled Divergent C4/C8 Site-Selective C–H Arylation of Isoquinolones

  摘要：

  The catalyst-controlled C4/C8 site-selective C-H arylation of isoquinolones using aryliodonium salts as the coupling partners was developed. The C4-selective arylation was successfully achieved via an electrophilic palladation pathway. A completely different selectivity pattern was observed using an Ir(III) catalytic system, which resulted in C-C bond formation exclusively at the C8 position. The isoquinolone scaffold can be conveniently equipped with various aryl substituents at either the C4 or C8 position.

  DOI：

  10.1021/acs.orglett.5b01840
• 作为产物：
  描述：

  二(4-氟苯基)碘嗡三氟甲磺酸盐 在 sodium hexaflorophosphate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 以91%的产率得到bis(4-fluorophenyl)iodonium hexafluorophosphate
  参考文献：
  名称：

  对映选择性铜催化芳基化驱动半频哪醇重排叔烯丙醇与二芳基碘盐

  摘要：

  报道了使用二芳基碘鎓盐对烯丙醇进行铜催化的对映选择性芳基化半频哪醇重排。手性 Cu(II)-双恶唑啉催化剂引发亲电烯烃芳基化，引发 1,2-烷基迁移，以提供一系列具有高产率、非对映选择性和对映选择性的非外消旋螺环酮。

  DOI：

  10.1021/jacs.7b05340

文献信息

• Copper(II)-Catalyzed Three-Component Cascade Annulation of Diaryliodoniums, Nitriles, and Alkynes: A Regioselective Synthesis of Multiply Substituted Quinolines
  作者：Yong Wang、Chao Chen、Jing Peng、Ming Li

  DOI：10.1002/anie.201300586

  日期：2013.5.10

  Three become one: Multiply substituted quinolines were synthesized from diaryliodoniums, alkynes, and nitriles by a CuII‐catalyzed method. This cascade annulation is highly regioselective, step‐economic, flexible with regard to the functional groups, and could potentially be applied to the synthesis of complex molecules.

  三合一：用Cu II催化方法从二芳基鎓，炔烃和腈中合成了被多取代的喹啉。这种级联环状结构具有高度的区域选择性，经济性，对功能基团的灵活性，可以潜在地应用于复杂分子的合成。
• Photocatalytic acylarylation of unactivated alkenes with diaryliodonium salts toward indanones and related compounds
  作者：Yongtao Chen、Chenyun Shu、Fang Luo、Xiaohui Xiao、Gangguo Zhu

  DOI：10.1039/c8cc02636j

  日期：——

  A novel photocatalytic acylarylation of unactivated alkenes using diaryliodonium salts as the arylation reagent is described. The reaction produces a variety of 2-benzyl indanones, 3,4-dihydronaphthalen-1(2H)-ones, and 2,3-dihydroquinolin-4(1H)-ones in promising yields with excellent diastereoselectivity under very mild conditions, which may be appealing for the synthesis of biologically active molecules

  描述了使用二芳基碘鎓盐作为芳基化试剂的未活化烯烃的新型光催化酰基芳基化。该反应可产生多种2-苄基茚满酮，3,4-二氢萘-1（2 H）-酮和2,3-二氢喹啉-4（1 H）-酮，并且在非常温和的条件下具有优异的非对映选择性，这可能对生物活性分子的合成很有吸引力。
• Cu-catalyzed intramolecular aryl-etherification reactions of alkoxyl alkynes with diaryliodonium salts via cleavage of a stable C–O bond
  作者：Jing Chen、Chao Chen、Junjie Chen、Guohua Wang、Hongmei Qu

  DOI：10.1039/c4cc08363f

  日期：——

  A novel Cu-catalyzed intramolecular aryl-etherification reaction of alkoxyl alkynes with diaryliodonium salts is realized. The reactions proceed smoothly to produce valuable oxo-heterocycles with readily available linear starting materials via cleavage of a stable C-O bond.

  实现了一种新型的铜催化的烷氧基炔烃与二芳基碘鎓盐的分子内芳基醚化反应。反应平稳进行，通过裂解稳定的CO键，生成具有容易获得的线性起始原料的有价值的氧杂环。
• Synthesis of 1-Thio-Substituted Isoquinoline Derivatives by Tandem Cyclization of Isothiocyanates
  作者：Li-Rong Wen、Qian Dou、Yuan-Chao Wang、Jin-Wei Zhang、Wei-Si Guo、Ming Li

  DOI：10.1021/acs.joc.6b02605

  日期：2017.2.3

  A copper-catalyzed tandem arylation–cyclization process to access 1-(arylthio)isoquinolines from isothiocyanates and diaryliodonium salts is described. It is the first general method to construct the potentially useful 1-(arylthio)isoquinoline derivatives. Moreover, 1-(methylthio)isoquinoline derivatives were also achieved successfully with MeOTf instead of diaryliodonium salts under metal-free conditions

  描述了一种铜催化的串联芳基化-环化过程，以从异硫氰酸盐和二芳基碘鎓盐中获得1-（芳硫基）异喹啉。构造潜在有用的1-（芳硫基）异喹啉衍生物是第一种通用方法。此外，在无金属条件下，用MeOTf代替二芳基碘鎓盐也成功获得了1-（甲硫基）异喹啉衍生物。机理研究表明，这两个过程以不同的方式进行。该方法已成功地应用于喹唑啉酮生物碱芸苔芸香碱的合成。
• Cu-Catalyzed Arylcarbocyclization of Alkynes with Diaryliodonium Salts through C–C Bond Formation on Inert C_(sp3)–H Bond
  作者：Jing Peng、Chao Chen、Junjie Chen、Xiang Su、Chanjuan Xi、Hui Chen

  DOI：10.1021/ol501655g

  日期：2014.7.18

  Copper-catalyzed arylcarbocyclization reaction of alkynes was realized with diaryliodonium salts through C-C bond formation on an inert C-(sp3)-H bond. This method provides an efficient cyclization of alkyl alkynes to generate carbocycles with good step-economy. Theoretical study revealed an interesting Cu-catalyzed concerted pathway of the C-C bond formation.