bis(4-bromophenyl)iodonium hexafluorophosphate | 1160481-37-7

• 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-bromophenyl)iodonium hexafluorophosphate
• 英文别名: Bis(4-bromophenyl)iodanium;hexafluorophosphate
• CAS: 1160481-37-7
• 化学式: C₁₂H₈Br₂I*F₆P
• 分子量: 583.872
• InChiKey: UUMMOHBCGWSGSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 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：
  7

反应信息

• 作为反应物：
  描述：

  2-甲基异喹啉-1(2H)-酮 、 bis(4-bromophenyl)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88%的产率得到8-(4-bromophenyl)-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-溴苯基)碘鎓三氟甲烷磺酸盐 在 六氟磷酸钾 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 bis(4-bromophenyl)iodonium hexafluorophosphate
  参考文献：
  名称：

  Cu-Catalyzed Arylcarbocyclization of Alkynes with Diaryliodonium Salts through C–C Bond Formation on Inert C_(sp3)–H Bond

  摘要：

  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.

  DOI：

  10.1021/ol501655g

文献信息

• Arylation of aryllithiums with <i>S</i>-arylphenothiazinium ions for biaryl synthesis
  作者：Tatsuya Morofuji、Tatsuki Yoshida、Ryosuke Tsutsumi、Masahiro Yamanaka、Naokazu Kano

  DOI：10.1039/d0cc05830k

  日期：——

  Aryllithiums were arylated with S-arylphenothiazinium ions through selective ligand coupling of intermediary sulfuranes. Various unsymmetrical biaryls were obtained without transition-metal catalysis.

  通过中间硫醚的选择性配体偶联，将芳基锂与S-芳基苯并噻嗪离子芳基化。在无过渡金属催化剂的情况下获得了各种非对称联苯。
• Synthesis of Quinoline Derivatives via Cu-Catalyzed Cascade Annulation of Heterocumulenes, Alkynes, and Diaryliodonium Salts
  作者：Yue Chi、Haihan Yan、Wen-Xiong Zhang、Zhenfeng Xi

  DOI：10.1021/acs.orglett.7b01025

  日期：2017.5.19

  cascade [2 + 2 + 2] and [4 + 2] annulation reactions among heterocumulenes, alkynes, and diaryliodonium salts were achieved. Various quinoline derivatives could be obtained in good yields with excellent selectivity. This methodology provided a novel pathway to activate heterocumulenes via a unique highly reactive cationic intermediate. The reaction process was well elucidated by density functional theory

  CuOTf催化的取代基控制的级联[2 + 2 + 2]和[4 + 2]杂铜烯，炔烃和二芳基碘鎓盐之间的环化反应得以实现。可以以高收率和优异的选择性获得各种喹啉衍生物。该方法学提供了一种通过独特的高反应性阳离子中间体激活杂聚枯烯的新颖途径。通过密度泛函理论计算很好地阐明了反应过程。
• 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 3-Iodoquinolines by Copper-Catalyzed Tandem Annulation from Diaryliodoniums, Nitriles, and 1-Iodoalkynes
  作者：Xuesong Wang、Xingyong Wang、Dayun Huang、Chulong Liu、Xinyan Wang、Yuefei Hu

  DOI：10.1002/adsc.201600081

  日期：2016.7.14

  A novel method for the synthesis of 3‐iodoquinolines was developed by copper‐catalyzed tandem annulation from diaryliodoniums, nitriles, and 1‐iodoalkynes. It is a method that is characterized by the most convenient operation and wide molecular diversity.

  通过铜催化串联从二芳基牙鎓，腈和1-碘代炔烃的环化反应，开发了一种新型的3-碘代喹啉合成方法。该方法以最方便的操作和广泛的分子多样性为特征。