4'-methoxybiphenyltosylate | 356031-48-6

• 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: 4'-methoxybiphenyltosylate
• 英文别名: 4′-methoxy-[1,1′-biphenyl]-4-yl 4-methylbenzenesulfonate；4'-methoxy-[1,1'-biphenyl]-4-yl 4-methylbenzenesulfonate；[4-(4-Methoxyphenyl)phenyl] 4-methylbenzenesulfonate
• CAS: 356031-48-6
• 化学式: C₂₀H₁₈O₄S
• 分子量: 354.427
• InChiKey: FWRCKUFXEMEBET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(三氟甲基)苯硼酸 、 4'-methoxybiphenyltosylate 在 potassium phosphate 、 二氯化双(三环己基膦)镍(II) 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 60.0h， 以81%的产率得到1-(4'-methoxyphenyl)-4-(3'-trifluoromethylphenyl)benzene
  参考文献：
  名称：

  NiCl₂(PCy₃)₂:  A Simple and Efficient Catalyst Precursor for the Suzuki Cross-Coupling of Aryl Tosylates and Arylboronic Acids

  摘要：

  [GRAPHICS]NiCl2(PCy3)(2) associated with PCy3 promotes the selective cross-coupling of aryltosylates with arylboronic acids under relatively mild reaction conditions, and a variety of functional groups are tolerated in both arenes. This is one of the simplest and most efficient experimental procedures for the coupling of arylboronic acids with aryl tosylates reported to date.

  DOI：

  10.1021/ol016526l
• 作为产物：
  描述：

  对甲苯磺酰氯 在 吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 potassium phosphate 、 二甲基苯基磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 4'-methoxybiphenyltosylate
  参考文献：
  名称：

  小膦配体使 Ar-O 在镍 (0) 上的 Ar-Cl 键上选择性氧化加成

  摘要：

  非三氟甲磺酸酯苯酚衍生物的 Suzuki-Miyaura 偶联的当前方法受限于它们对卤化物（包括芳基氯）的不耐受性。这是因为 Ni(0) 和 Pd(0) 通常以与大多数 Ar-O 键相似或更快的速率进行有机卤化物的氧化加成。DFT 和化学计量氧化加成研究表明，小膦，特别是 PMe3，在促进 Ni(0) 与芳基甲苯磺酸酯和其他 CO 键在芳基氯化物存在下的优先反应方面是独一无二的。这种选择性在第一个 Ni 催化的 CO 选择性 Suzuki-Miyaura 偶联氯化苯酚衍生物中得到了利用，其中含氧离去基团不是氟化磺酸盐，例如三氟甲磺酸盐。计算研究表明，PMe3 和其他膦之间发散选择性的起源不同于配体控制的化学发散交叉偶联的先前例子。由于电子和空间因素，PMe3 影响甲苯磺酸盐的选择性反应。在氧化加成过程中镍和甲苯磺酸的磺酰氧之间的密切相互作用对观察到的选择性至关重要。

  DOI：

  10.1021/jacs.0c06995

文献信息

• Unified Protocol for Fe-Based Catalyzed Biaryl Cross-Couplings between Various Aryl Electrophiles and Aryl Grignard Reagents
  作者：Lei Wang、Yi-Ming Wei、Yan Zhao、Xin-Fang Duan

  DOI：10.1021/acs.joc.9b00151

  日期：2019.5.3

  Ti(OEt)4/PhOM enabled a highly general iron-based catalyst system, which could efficiently catalyze the biaryl coupling reaction between various electrophiles (I, Br, Cl, OTs, OCONMe2, OSO2NMe2) and common or functionalized aryl Grignard reagents with high functional group tolerance. Selective couplings of aryl iodides and bromides over the corresponding oxygen-based electrophiles have been achieved, and

  常用的FeCl 3 / SIPr与Ti（OEt）4 / PhOM的组合可实现高度通用的铁基催化剂体系，该体系可有效催化各种亲电试剂（I，Br，Cl，OTs，OCONMe 2， OSO 2 NMe 2）和具有高官能团耐受性的常用或官能化芳基格氏试剂。已经实现了芳基碘化物和溴化物在相应的基于氧的亲电试剂上的选择性偶联，因此，通过正交偶联策略方便地合成了阿尼芬净的三联苯甲酸中间体。
• Palladium-Catalyzed Hiyama Cross-Couplings of Aryl Arenesulfonates with Arylsilanes
  作者：Liang Zhang、Jie Wu

  DOI：10.1021/ja804672m

  日期：2008.9.17

  Palladium-catalyzed efficient Hiyama cross-coupling reaction of aryl arenesulfonate with arylsilane is described. The desired carbon-carbon bond formation proceeds under mild conditions with good functional group tolerance.

  描述了钯催化的芳基芳烃磺酸酯与芳基硅烷的高效 Hiyama 交叉偶联反应。所需的碳-碳键形成在温和条件下进行，具有良好的官能团耐受性。
• Palladium-Catalyzed Cross-Electrophile Coupling between Aryl Diazonium Salt and Aryl Iodide/Diaryliodonium Salt in H₂O–EtOH
  作者：Kartic Manna、Ranjan Jana

  DOI：10.1021/acs.orglett.2c03932

  日期：2023.1.20

  chemoselective palladium-catalyzed cross-electrophile coupling between readily accessible aromatic diazonium salt and aryl iodide or diaryliodonium salt in water–ethanol (2:1) medium. Mechanistic studies revealed that ethanol is crucial to generate an active Pd(0) catalyst, and the counterion of the diazonium salt renders a cationic Pd(II) species that facilitates subsequent oxidative addition to aryl iodide/diaryliodonium

  我们在此报告了一种温和的高度化学选择性钯催化的交叉亲电试剂偶联，该反应在水-乙醇 (2:1) 介质中容易获得的芳香族重氮盐和芳基碘化物或二芳基碘盐之间发生。机理研究表明，乙醇对于产生活性 Pd(0) 催化剂至关重要，而重氮盐的抗衡离子呈现阳离子 Pd(II) 物质，促进随后氧化加成到芳基碘化物/二芳基碘盐。银 (I) 盐对于保留钯的催化活性至关重要，它可以去除沉淀物中的碘离子。
• ADSORBENT FOR REMOVING HISTONE AND PURIFICATION DEVICE FOR LIQUID DERIVED FROM LIVING ORGANISM
  申请人：ASAHI KASEI MEDICAL CO., LTD.

  公开号：US20170173231A1

  公开（公告）日：2017-06-22

  Provided is an adsorbent for removing histones from a liquid derived from a living-organism, including a water-insoluble carrier and a biocompatible polymer. The carrier has activated carbon, a polyester, a polysulfone, or a cationic functional group. Also provided is a device for purifying a liquid derived from a living-organism to remove histones from a liquid derived from a living-organism, which has a housing equipped with an inlet and an outlet for the liquid derived from the living-organism and the above-described adsorbent housed in the housing. The liquid derived from the living-organism is moved through the housing of device for purifying the liquid derived from the living-organism to remove histones from the liquid derived from the living-organism.
• NiCl₂(PCy₃)₂:  A Simple and Efficient Catalyst Precursor for the Suzuki Cross-Coupling of Aryl Tosylates and Arylboronic Acids
  作者：Danilo Zim、Vanusa R. Lando、Jairton Dupont、Adriano L. Monteiro

  DOI：10.1021/ol016526l

  日期：2001.9.1

  [GRAPHICS]NiCl2(PCy3)(2) associated with PCy3 promotes the selective cross-coupling of aryltosylates with arylboronic acids under relatively mild reaction conditions, and a variety of functional groups are tolerated in both arenes. This is one of the simplest and most efficient experimental procedures for the coupling of arylboronic acids with aryl tosylates reported to date.