N-(3-iodo-2-methylphenyl)-N,4-dimethylbenzenesulfonamide | 913548-99-9

• 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-(3-iodo-2-methylphenyl)-N,4-dimethylbenzenesulfonamide
• CAS: 913548-99-9
• 化学式: C₁₅H₁₆INO₂S
• 分子量: 401.268
• InChiKey: HPISSKPRJWBCNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-iodo-2-methylphenyl)-N,4-dimethylbenzenesulfonamide 、 3-(2-溴乙基)噻吩 在 降冰片烯 、 三(2-呋喃基)膦 、 palladium diacetate 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 以66%的产率得到N,4-dimethyl-N-(9-methyl-4,5-dihydronaphtho[1,2-b]thien-8-yl)benzenesulfonamide
  参考文献：
  名称：

  A Palladium-Catalyzed Approach to Polycyclic Sulfur Heterocycles

  摘要：

  The synthesis of a variety of polycyclic thiophenes and benzothiophenes is accomplished via a palladium-catalyzed domino ortho-alkylation/direct arylation reaction. An examination of the intramolecular direct arylation of thiophenes suggests that an electrophilic metalation mechanism may be present. This method was further extended to include the synthesis of a (thieno)benzoxepine.

  DOI：

  10.1021/jo8020105
• 作为产物：
  描述：

  2-氨基-6-碘甲苯 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-(3-iodo-2-methylphenyl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  钯催化的降冰片烯介导的串联胺化/氰化反应：一种合成邻氨基苯甲腈的方法

  摘要：

  通过使用N-苯甲酰氧基胺作为胺化试剂和Zn（CN）2作为终止剂，开发了通过卡塞拉尼型C–H官能化进行的钯催化，降冰片烯介导的串联胺化/氰化反应。这种形成一个C–N键和一个C–C键的转变，为从容易获得的起始原料在一锅中合成邻氨基苯甲腈提供了一种有效的方法。

  DOI：

  10.1021/acs.orglett.6b02249

文献信息

• Palladium-Catalyzed Cascade CH Trifluoroethylation of Aryl Iodides and Heck Reaction: Efficient Synthesis of<i>ortho</i>-Trifluoroethylstyrenes
  作者：Hao Zhang、Pinhong Chen、Guosheng Liu

  DOI：10.1002/anie.201403793

  日期：2014.9.15

  A palladium‐catalyzed selective CH bond trifluoroethylation of aryl iodides has been explored. The reaction allows for the efficient synthesis of a variety of ortho‐trifluoroethyl‐substituted styrenes. Preliminary mechanistic studies indicate that the reaction might involve a key PdIV intermediate, which is generated through the rate‐determining oxidative addition of CF3CH2I to a palladacycle; the

  已探索了钯催化的芳基碘化物的选择性CH键三氟乙基化。该反应可有效合成多种邻三氟乙基取代的苯乙烯。初步的机理研究表明，该反应可能涉及关键的Pd IV中间体，该中间体是通过速率确定CF 3 CH 2 I氧化成palladacycle生成的。CF 3 CH 2 I的大体积性质影响反应性。然后从Pd IV络合物中进行还原性消除会导致形成芳基-CH 2 CF 3键。
• A Convergent Synthesis of Polysubstituted Aromatic Nitriles via Palladium-Catalyzed C−H Functionalization
  作者：Brian Mariampillai、Julien Alliot、Mengzhou Li、Mark Lautens

  DOI：10.1021/ja075599i

  日期：2007.12.1

  A palladium-catalyzed C-H functionalization reaction for the synthesis of highly substituted aromatic nitriles is reported. The modularity of the reaction is demonstrated by the broad range of aryl iodides which can be coupled with metal cyanides and alkyl halides or aryl bromides.

  报道了一种钯催化的 CH 官能化反应，用于合成高度取代的芳香腈。广泛的芳基碘化物可以与金属氰化物和烷基卤化物或芳基溴化物偶联，证明了该反应的模块化。
• Synthesis of Annulated 2<i>H</i>-Indazoles and 1,2,3- and 1,2,4-Triazoles via a One-Pot Palladium-Catalyzed Alkylation/Direct Arylation Reaction
  作者：Benoît Laleu、Mark Lautens

  DOI：10.1021/jo8017236

  日期：2008.11.21

  A variety of six-membered-ring annulated 2H-indazoles and 1,2,3- and 1,2,4-triazoles were synthesized in good to excellent yields from the corresponding bromoethyl azoles and aryl iodides. The annulation process involves a one-pot norbornene-mediated palladium-catalyzed sequence whereby an alkyl-aryl bond and an aryl-heteroaryl bond are successively formed through two C-H bond activations. Subsequent

  从相应的溴乙基唑和芳基碘化物以良好至优异的收率合成了多种六元环环状的2H-吲唑以及1,2,3-和1,2,4-三唑。环合过程涉及一锅降冰片烯介导的钯催化的序列，其中烷基-芳基键和芳基-杂芳基键通过两次CH键激活连续形成。还介绍了通过交叉偶联反应对所得多环化合物的后续官能化作用。
• Synthesis of Polycyclic Heterocycles via a One-Pot Ortho Alkylation/Direct Heteroarylation Sequence
  作者：Andrew Martins、Dino Alberico、Mark Lautens

  DOI：10.1021/ol061859+

  日期：2006.10.1

  Polycyclic thiophenes and furans were synthesized using a one-pot ortho alkylation/direct heteroarylation reaction sequence. Under the optimized reaction conditions, aryl iodides were coupled with 3-(bromoalkyl) thiophenes or -furans, affording six-and seven-membered annulated ring products via formation of two C-C bonds from two aryl C-H bonds.
• Palladium-Catalyzed Norbornene-Mediated Tandem Amination/Cyanation Reaction: A Method for the Synthesis of <i>ortho</i>-Aminated Benzonitriles
  作者：Bo Luo、Jin-Ming Gao、Mark Lautens

  DOI：10.1021/acs.orglett.6b02249

  日期：2016.9.2

  norbornene-mediated tandem amination/cyanation reaction via Catellani-type C–H functionalization was developed using N-benzoyloxyamines as the amination reagent and Zn(CN)2 as the terminating agent. This transformation, in which one C–N bond and one C–C bond are formed, provides an efficient approach for the synthesis of ortho-aminated benzonitriles in one pot from easily accessible starting materials

  通过使用N-苯甲酰氧基胺作为胺化试剂和Zn（CN）2作为终止剂，开发了通过卡塞拉尼型C–H官能化进行的钯催化，降冰片烯介导的串联胺化/氰化反应。这种形成一个C–N键和一个C–C键的转变，为从容易获得的起始原料在一锅中合成邻氨基苯甲腈提供了一种有效的方法。