tert-butyl 4'-methoxy-biphenyl-4-carboxylate | 944385-73-3

• 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: tert-butyl 4'-methoxy-biphenyl-4-carboxylate
• 英文别名: tert-butyl 4'-methoxy-4-biphenylcarboxylate；4-tert-butoxycarbonyl-4'-methoxy-1,1'-biphenyl；tert-butyl 4-(4-methoxyphenyl)benzoate
• CAS: 944385-73-3
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: CLUMDQLLEGMGHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  Tert-butyl 4-(trifluoromethylsulfanyl)benzoate 在 ruthenium trichloride 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 C₃₈H₅₄Cl₂N₄Pd 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 14.08h， 生成 tert-butyl 4'-methoxy-biphenyl-4-carboxylate
  参考文献：
  名称：

  钯/铑协同催化下芳基三氟甲基砜与芳基硼酸酯的交叉偶联

  摘要：

  经由C-SO 2键裂解的Suzuki-Miyaura芳基三氟甲基砜芳基化反应是通过钯/铑协同催化方法开发的。将一系列芳基三氟甲基砜和芳基硼酸新戊基二醇酯转化为相应的联芳基。机理研究表明：（1）铑催化剂介导芳基环从芳基硼酸酯到钯的转移，从而加速了过渡金属化步骤，（2）形成C–C键的还原性消除步骤是限制营业额的步。

  DOI：

  10.1021/acs.orglett.9b03393

文献信息

• Palladium‐catalysed room‐temperature Suzuki–Miyaura coupling in water extract of pomegranate ash, a bio‐derived sustainable and renewable medium
  作者：Rama Moorhy Appa、S. Siva Prasad、Jangam Lakshmidevi、Bandameeda Ramesh Naidu、Manchala Narasimhulu、Katta Venkateswarlu

  DOI：10.1002/aoc.5126

  日期：2019.10

  the first time as a renewable medium for Pd(OAc)2‐catalysed Suzuki–Miyaura cross‐coupling at room temperature. This method offers a simple and sustainable synthesis of biaryls from aryl halides and arylboronic acids under ligand‐ and external base‐free aerobic and ambient conditions. This method has been found effective for both activated and unactivated aryl halides in the production of biaryls with

  源自农业废物的“石榴灰水提取物”（WEPA）首次用作Pd（OAc）2的可再生介质在室温下催化的Suzuki-Miyaura交叉偶联。该方法可在配体和无碱无氧和环境条件下，从芳基卤化物和芳基硼​​酸简单，可持续地合成联芳基。已经发现该方法对联芳烃的生产中活化和未活化的芳基卤化物均有效，产率中等至几乎定量。该方案显示出在芳基卤化物中相同/相似的反应位上具有较高的化学选择性（即，在芳基卤化物的相同卤素或不同卤素上具有选择性）。该方法表现出高的区域选择性，即卤素对芳族核上不同位置上的其他相同卤素的选择性反应性。因此，我们在此披露干净，良性，
• An Improvement of Nickel Catalyst for Cross-coupling Reaction of Arylboronic Acids with Aryl Carbonates by Using a Ferrocenyl Bisphosphine Ligand
  作者：Ryoichi Kuwano、Ryosuke Shimizu

  DOI：10.1246/cl.2011.913

  日期：2011.9.5

  Aryl carbonates work as electrophilic substrates for the Suzuki–Miyaura reaction in the presence of the nickel catalyst, which is generated from [Ni(cod)2] and ferrocenyl bisphosphine, DCyPF. The nickel catalyst allowed the cross-coupling reaction of arylboronic acids with non-benzo-fused aryl carbonates as well as naphthyl substrates.

  芳基碳酸酯在镍催化剂存在下，作为铃木–宫浦反应的电亲体底物，该催化剂由[Ni(cod)2]和铁烯基双磷酸酯DCyPF生成。镍催化剂促进了芳基硼酸与非苯并融合的芳基碳酸酯以及萘基底物的交叉偶联反应。
• Suzuki–Miyaura Cross-Coupling of 1,8-Diaminonaphthalene (dan)-Protected Arylboronic Acids
  作者：Yuichiro Mutoh、Kensuke Yamamoto、Shinichi Saito

  DOI：10.1021/acscatal.9b03667

  日期：2020.1.3

  Suzuki–Miyaura cross-coupling reaction of 1,8-diaminonaphthalene (dan)-protected arylboronic acids in the presence of KOt-Bu, which does not require the removal of the dan moiety. Notably, the use of aryl-B(dan) in the Suzuki–Miyaura reaction provides a complementary solution to the protodeboronation problems. The base KOt-Bu plays a crucial role for the promotion of these cross-coupling reactions as

  我们报道了在存在KO t -Bu的情况下1,8-二氨基萘（dan）保护的芳基硼酸的Suzuki-Miyaura交叉偶联反应，该反应不需要去除dan部分。值得注意的是，在Suzuki-Miyaura反应中使用芳基-B（dan）可为原脱硼问题提供补充解决方案。碱KO t -Bu在促进这些交叉偶联反应中起着至关重要的作用，因为它能够形成硼酸盐。该反应方案扩展到了4-[（（pin）B] C 6 H 4 -B（dan）的一锅顺序Suzuki-Miyaura交叉偶联反应，其中“反应性较低”的芳基-B（dan）部分优先交叉耦合。
• Practical One-Pot Preparation of Magnesium Di(hetero)aryl- and Magnesium Dialkenylboronates for Suzuki-Miyaura Cross-Coupling Reactions
  作者：Benjamin A. Haag、Christoph Sämann、Anukul Jana、Paul Knochel

  DOI：10.1002/anie.201103022

  日期：2011.8.1

  Mg for B: An atom‐economical one‐pot synthesis by direct magnesium insertion in the presence of B(OBu)3 and LiCl allows a broad range of functionalized (hetero)aryl and alkenyl bromides to be converted into magnesium diorganoboronates 2, which undergo Suzuki–Miyaura cross‐coupling reactions with various aryl (pseudo)halides (see scheme). Both aryl groups of 2 are transferred and furnish the products

  毫克乙：一个原子经济一锅合成通过在B存在（OBU）直接镁插入3和LiCl允许宽范围的官能化的（杂）芳基和链烯基溴化物以转换成镁diorganoboronates 2，其经历Suzuki-Miyaura与各种芳基（假）卤化物的交叉偶联反应（参见方案）。的两个芳基2被转印并在良好的产品提供优异的产率。
• Phosphine oxides as stabilizing ligands for the palladium-catalyzed cross-coupling of potassium aryldimethylsilanolates
  作者：Scott E. Denmark、Russell C. Smith、Steven A. Tymonko

  DOI：10.1016/j.tet.2007.02.017

  日期：2007.6

  The palladium-catalyzed cross-coupling reaction of potassium (4-methoxyphenyl) dimethylsilanolate (K(+)1(-)) with aryl bromides has been demonstrated using triphenylphosphine oxide as a stabilizing ligand. Unsymmetrical biaryls can be prepared from a variety of aryl bromides in good yield with short reaction times. Qualitative kinetic studies compared effects of different phosphine oxides on the rate of cross-coupling and established the beneficial effect of these ligands in the reaction of electron-rich arylsilanolates. The improved yield and reproducibility of the cross-coupling of several bromides was demonstrated by direct comparison of reactions performed with and without triphenylphosphine oxide under non-rigorous exclusion of oxygen. (C) 2007 Elsevier Ltd. All rights reserved.