N-(2-bromo-5-chlorophenyl)-4-methylbenzenesulfonamide

• 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-(2-bromo-5-chlorophenyl)-4-methylbenzenesulfonamide
• 化学式: C₁₃H₁₁BrClNO₂S
• mdl: MFCD23545931
• 分子量: 360.659
• InChiKey: GAFANULLYWTRQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-bromo-5-chlorophenyl)-4-methylbenzenesulfonamide 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 [Ir(ppy)₂bpy]PF₆ 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Visible-Light-Driven Neutral Nitrogen Radical Mediated Intermolecular Styrene Difunctionalization

  摘要：

  A neutral nitrogen radical-mediation strategy, wherein the existing N-H moiety of substrates serves as a neutral nitrogen radical precursor to enable room-temperature intermolecular radical difunctionalization of styrenes under photoredox catalysis, is reported. The reaction shows high functional group tolerance and substrate scope with respect to both components, giving the corresponding products with generally good yields. Preliminary control experiments and DFT calculations are performed to explain the reaction mechanism.

  DOI：

  10.1021/acs.orglett.9b01362
• 作为产物：
  描述：

  2-溴-5-氯苯胺 、 对甲苯磺酰氯 在 吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 0.17h， 生成 N-(2-bromo-5-chlorophenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Visible-Light-Driven Neutral Nitrogen Radical Mediated Intermolecular Styrene Difunctionalization

  摘要：

  A neutral nitrogen radical-mediation strategy, wherein the existing N-H moiety of substrates serves as a neutral nitrogen radical precursor to enable room-temperature intermolecular radical difunctionalization of styrenes under photoredox catalysis, is reported. The reaction shows high functional group tolerance and substrate scope with respect to both components, giving the corresponding products with generally good yields. Preliminary control experiments and DFT calculations are performed to explain the reaction mechanism.

  DOI：

  10.1021/acs.orglett.9b01362

文献信息

• An Efficient One-Pot Synthesis of Benzo[4,5]imidazo[1,2-<i>a</i>]quinoxalines <i>via</i> Copper-Catalyzed Process
  作者：Aiping Huang、Yimu Chen、Yige Zhou、Wei Guo、Xiaodong Wu、Chen Ma

  DOI：10.1021/ol4026292

  日期：2013.11

  A copper-catalyzed one-pot process for the construction of benzo[4,5]imidazo[1,2-a]quinoxalines under air is described. Aryl chlorides, aryl bromides, and aryl iodides can be applied to the synthesis of these compounds.

  描述了在空气下构造苯并[4,5]咪唑并[1,2- a ]喹喔啉的铜催化一锅法。芳基氯化物，芳基溴化物和芳基碘化物可用于这些化合物的合成。
• Enantioselective Desymmetrization of Cyclobutanones Enabled by Synergistic Palladium/Enamine Catalysis
  作者：Meng Wang、Jun Chen、Zongjia Chen、Changxu Zhong、Ping Lu

  DOI：10.1002/anie.201711845

  日期：2018.3.1

  The enantioselective intramolecular α‐arylation of cyclobutanones has been established by combining palladium and enamine catalyst systems. Two different enantioselective control strategies have been developed for cyclobutanone substrates bearing O‐ or N‐tethered aryl bromides. Further synthetic applications are also reported.

  通过结合钯和烯胺催化剂体系，建立了环丁酮的对映选择性分子内α-芳基化反应。对于带有O或N系芳基溴化物的环丁酮底物，已经开发出两种不同的对映选择性控制策略。还报道了进一步的合成应用。
• Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization of norbornene and norbornadiene
  作者：Mengna Tao、Wenbo Li、Junliang Zhang

  DOI：10.1039/d0cc04996d

  日期：——

  to various chiral norbornane-fused dihydrofurans and dihydro-pyrroles. This synthetic methodology provides the first example of asymmetric carboetherification of norbornene, and also tolerates norbornadiene well.

  描述了降冰片烯的高对映选择性的Pd / Xiang-Phos催化的碳杂碳官能化，可直接获得各种手性降冰片烷稠合的二氢呋喃和二氢吡咯。这种合成方法学提供了降冰片烯不对称碳醚化的第一个例子，也很好地耐受了降冰片二烯。
• Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization under mild conditions
  作者：Mengna Tao、Youshao Tu、Yu Liu、Haihong Wu、Lu Liu、Junliang Zhang

  DOI：10.1039/d0sc01391a

  日期：——

  enantioselective intermolecular carboheterofunctionalization reaction of 2,3-dihydrofurans is developed, leading to various optically active fused furoindolines and tetrahydrofurobenzofurans. The key to this transformation is employing two newly modified N-Me-Xiang-Phos ligands ((S, RS)-N-Me-X4/X5) as chiral ligands under mild conditions. Moreover, this synthetic methodology can be efficiently applied to a variety

  开发了一种温和实用的 Pd/象磷催化的 2,3-二氢呋喃对映选择性分子间碳杂官能化反应，产生各种光学活性的稠合呋喃吲哚啉和四氢呋喃苯并呋喃。这一转化的关键是在温和条件下采用两个新修饰的N -Me-Xiang-Phos配体(( S , RS ) -N -Me-X4 / X5 )作为手性配体。此外，通过在呋喃环上引入多种取代基，这种合成方法可以有效地应用于各种具有高化学、区域和对映选择性的复杂多取代杂环，而呋喃环上很难通过其他途径获得这些取代基。
• Pd-Catalyzed Heteroannulation Using <i>N</i>-Arylureas as a Sterically Undemanding Ligand Platform
  作者：Jakub Vaith、Dasha Rodina、Gregory C. Spaulding、Shauna M. Paradine

  DOI：10.1021/jacs.2c01019

  日期：2022.4.20