N-(5-bromothiophen-2-yl)-N-(phenylsulfonyl)benzenesulfonamide | 1453101-15-9

• 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: N-(5-bromothiophen-2-yl)-N-(phenylsulfonyl)benzenesulfonamide
• 英文别名: N-(benzenesulfonyl)-N-(5-bromothiophen-2-yl)benzenesulfonamide
• CAS: 1453101-15-9
• 化学式: C₁₆H₁₂BrNO₄S₃
• 分子量: 458.378
• InChiKey: PDDUQQOPIORYTI-UHFFFAOYSA-N

物化性质

• 沸点：
  601.0±65.0 °C(Predicted)
• 密度：
  1.682±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(phenylsulfonyl)-N-(thiophen-2-yl)benzenesulfonamide 在 1,3-二溴-5,5-二甲基海因 作用下， 以 1,2-二氯乙烷 为溶剂， 以24%的产率得到N-(5-bromothiophen-2-yl)-N-(phenylsulfonyl)benzenesulfonamide
  参考文献：
  名称：

  C–H Imidation and Dual C–H Bond Aminobromination of Five-Membered Heterocycles

  摘要：

  Here, we report a practical C-H imidation of five-membered heterocycles under metal-free conditions. We also report the first dual C-H bond aminobromination of thiophenes, with benzotriazole, saccharin, 1,2,4-triazole, benzimidazole, pyrazole, 4-bromopyrazole, 5-methyltetrazole, and dibenzenesulfonimides as effective amine sources. Mechanistic studies support the radical pathway of the imidation and aminobromination reactions.

  DOI：

  10.1021/acs.joc.9b02941

文献信息

• [EN] TRANSITION METAL-CATALYZED IMIDATION OF ARENES<br/>[FR] IMIDATION D'ARÈNES CATALYSÉE PAR DES MÉTAUX DE TRANSITION
  申请人：HARVARD COLLEGE

  公开号：WO2015031725A1

  公开（公告）日：2015-03-05

  The present invention provides novel transition metal complexes (e.g., complexes of any one of Formulae (C1) to (C25)) that include an amine-N-oxide motif. The invention also provides methods of using these transition metal complexes in preparing N-aryl or N- heteroaryl sulfonimides (e.g., compounds of Formula (I)) and aryl or heteroaryl amines (e.g., compounds of Formula (II)). The inventive methods involve imidation of arenes and heteroarenes (e.g., compounds of Formula (A)) using an imidating agent (e.g., a compound of Formula (B), such as N-fluorobenzenesulfonimide (NFBS or NFSI)) in the presence of a single-electron reductant (e.g., an Ag(I) or Ru(II) salt).

  本发明提供了新型过渡金属配合物（例如，任一公式（C1）至（C25）中的配合物），其中包括胺-N-氧化物基团。该发明还提供了使用这些过渡金属配合物制备N-芳基或N-杂芳基磺酰亚胺（例如，公式（I）中的化合物）和芳基或杂芳基胺（例如，公式（II）中的化合物）的方法。创新方法涉及使用一种咪唑化试剂（例如，公式（B）中的化合物，如N-氟苯磺酰亚胺（NFBS或NFSI））在单电子还原剂（例如，Ag(I)或Ru(II)盐）存在下对芳烃和杂芳烃（例如，公式（A）中的化合物）进行咪唑化。
• Catalytic C–H Imidation of Aromatic Cores of Functional Molecules: Ligand-Accelerated Cu Catalysis and Application to Materials- and Biology-Oriented Aromatics
  作者：Takahiro Kawakami、Kei Murakami、Kenichiro Itami

  DOI：10.1021/ja5130012

  日期：2015.2.25

  Versatile imidation of aromatic C-H bonds was accomplished. In the presence of copper bromide and 6,6'-dimethyl-2,2'-bipyridyl, a range of aromatics, such as polycyclic aromatic hydrocarbons, aromatic bowls, porphyrins, heteroaromatics, and natural products, can be imidated by N-fluorobenzenesulfonimide. A dramatic ligand-accelerated copper catalysis and an interesting kinetic profile were uncovered.
• Pd-Catalyzed Aryl C–H Imidation with Arene as the Limiting Reagent
  作者：Gregory B. Boursalian、Ming-Yu Ngai、Katarzyna N. Hojczyk、Tobias Ritter

  DOI：10.1021/ja4064926

  日期：2013.9.11

  An amine-N-oxide-ligated palladium complex, in conjunction with a silver cocatalyst, catalyzes imidation of arenes by the reagent N-fluorobenzenesulfonimide. The reaction enables imidation of a variety of arenes at or below room temperature, requires no coordinating directing group on the substrate, and gives synthetically useful yields with only 1 equiv of arene. Mechanistic data implicate an unusual mechanism devoid of commonly invoked organometallic intermediates: oxidation of the Pd catalyst occurs as the turnover-limiting step, while C-H bond functionalization occurs subsequently at a high oxidation state of the catalyst.
• C–H Imidation and Dual C–H Bond Aminobromination of Five-Membered Heterocycles
  作者：Kai Sun、Yali Li、Ranran Feng、Shiqiang Mu、Xin Wang、Bing Zhang

  DOI：10.1021/acs.joc.9b02941

  日期：2020.1.17

  Here, we report a practical C-H imidation of five-membered heterocycles under metal-free conditions. We also report the first dual C-H bond aminobromination of thiophenes, with benzotriazole, saccharin, 1,2,4-triazole, benzimidazole, pyrazole, 4-bromopyrazole, 5-methyltetrazole, and dibenzenesulfonimides as effective amine sources. Mechanistic studies support the radical pathway of the imidation and aminobromination reactions.