4'-chloro-2,6-dimethoxybiphenyl | 938764-37-5

• 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'-chloro-2,6-dimethoxybiphenyl
• 英文别名: 4’-chloro-2,6-dimethoxybiphenyl；2-(4-Chlorophenyl)-1,3-dimethoxybenzene
• CAS: 938764-37-5
• 化学式: C₁₄H₁₃ClO₂
• 分子量: 248.709
• InChiKey: DQWAKSGPYBKTII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯碘苯 、 2,6-二甲氧基苯硼酸 在 C₂₃H₃₄Cl₂N₄O₃Pd 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 以92%的产率得到4'-chloro-2,6-dimethoxybiphenyl
  参考文献：
  名称：

  ADC-Based Palladium Catalysts for Aqueous Suzuki–Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems

  摘要：

  The reaction between the equimolar amounts of cis-[PdCl2(CNR1)(2)] (R-1 = cyclohexyl (Cy) (1), tBu (2)) and the carbohydrazides (RCONHNH2)-C-2 (R-2 = Ph (5), 4-ClC6H4 (6), 3-NO2C6H4 (7), 4-NO2C6H4 (8), 4-CH3C6H4 (9), 3,4-(MeO)(2)C6H3 (10), naphth-1-yl (11), fur-2-yl (12), 4-NO2C6H4CH2 (13), Cy (14), 1-(4-fluorophenyl)-5-oxopyrrolidin-3-yi (15), (pyrrolidin-1-yl)C(0) (16)) proceeds in refluxing CHCl3 for ca. 4 h. A subsequent workup provided the amino-carbene species cis-[PdCl2{C(NHNHC(O)R-2)=N(H)R-1}-(CNR1)] (18-33) in good to excellent (80-95%) isolated yields. The coupling of equimolar amounts of cis-[PdCl2(CNR1)(2)] (R-1 = Cy (1), tBu (2), 2,6-Me2C6H3 (XYI) (3), 2-Cl-6-MeC6H3 (4)) and PhSO2NHNH2 (17) occurs similarly and affords the aminocarbenes cis-[PdCl2{C(NHNHS(O)(2)Ph)=N(H)R-1}(CNR1)] (34-37; 60-90%). Complexes 18-37 were characterized by elemental analyses (C, H, N), ESV+-MS, IR, and 1D (H-1, C-13{H-1}) and 2D (H-1,H-1-COSY, H-1,C-13-HMQC, H-1,C-13-HSQC, HMBC) NMR spectroscopy, as well as by X-ray diffraction for three species (34, 37, and 38). The catalytic properties of 18-37 in Suzuki Miyaura cross-coupling in aqueous medium were evaluated, and 18-37 showed remarkable activity (0.001-0.01 mol % catalyst loading). The scope of the catalytic process covers sterically unhindered and sterically demanding aryl bromides and aryl iodides bearing donor and/or acceptor substituents and activated aryl chlorides. All organohalides reacted with a range of arylboronic acids at 80 degrees C within 2 h (100 degrees C and 3 h for the chlorides), providing target diaryis in yields up to 99% and with maximum TONs of 9.9 X 10(3) (for aryl iodides), 4.7 X 104 (for aryl bromides), and 9.2 X 10(3) (for aryl chlorides).

  DOI：

  10.1021/om4007592

文献信息

• Synthesis of Biaryls via Decarboxylative Pd-Catalyzed Cross-Coupling Reaction
  作者：Jean-Michel Becht、Cédric Catala、Claude Le Drian、Alain Wagner

  DOI：10.1021/ol070495y

  日期：2007.4.1

  and efficient route to biaryls via Pd-catalyzed decarboxylative cross-couplings of arene carboxylic acids and aryl iodides is reported. The PdCl2/AsPh3 catalytic system in the presence of Ag2CO3 in DMSO was found to be particularly efficient to perform this transformation. This reaction can be extended to the synthesis of various biaryls, including sterically hindered biaryls, with yields ranging from

  [反应：见正文]据报道，通过芳烃羧酸和芳基碘化物的Pd催化脱羧交叉偶联，可以简单有效地制得联芳基。发现在DMSO中存在Ag2CO3的情况下，PdCl2 / AsPh3催化体系特别有效。该反应可以扩展到包括空间位阻联芳基的各种联芳基的合成，产率为58％至90％。
• Murahashi Cross‐Coupling at −78 °C: A One‐Pot Procedure for Sequential C−C/C−C, C−C/C−N, and C−C/C−S Cross‐Coupling of Bromo‐Chloro‐Arenes
  作者：Narayan Sinha、Dorus Heijnen、Ben L. Feringa、Michael G. Organ

  DOI：10.1002/chem.201901678

  日期：2019.7.11

  The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as −78 °C) has been achieved with high‐reactivity Pd‐NHC catalysts. A temperature‐dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one‐pot, sequential coupling strategy is presented for the

  使用高反应性的Pd-NHC催化剂可以在低温（低至-78°C）下偶联有机锂试剂（包括受阻实例）。已开发出一种温度依赖性的化学选择性触发器，用于在氯化物存在下选择性偶联芳基溴化物。在此基础上，提出了一种用于快速构建高级构建基块的单锅顺序耦合策略。重要的是，已经实现了将烷基锂化合物一次性添加到Pd交叉偶联反应中，从而无需通过注射泵缓慢添加。
• Pd-catalysed decarboxylative Suzuki reactions and orthogonal Cu-based O-arylation of aromatic carboxylic acids
  作者：Jian-Jun Dai、Jing-Hui Liu、Dong-Fen Luo、Lei Liu

  DOI：10.1039/c0cc04104a

  日期：——

  Pd-catalysed decarboxylative Suzuki reactions and orthogonal Cu-based O-arylation reactions of aromatic carboxylic acids are reported. The new reactions may provide alternative routes for the synthesis of some biaryls and aromatic carboxylic esters.

  钯催化的脱羧Suzuki反应和芳香族羧酸的正交Cu基O-芳基化反应已有报道。新的反应可能为某些联芳基和芳族羧酸酯的合成提供替代途径。
• Low-Temperature Ag/Pd-Catalyzed Decarboxylative Cross-Coupling of Aryl Triflates with Aromatic Carboxylate Salts
  作者：Lukas J. Gooßen、Paul P. Lange、Nuria Rodríguez、Christophe Linder

  DOI：10.1002/chem.200903319

  日期：2010.4.6

  At 50°C lower than the best known copper catalysts, a catalytic silver(I)/palladium(II) system allows the decarboxylative cross‐coupling of arenecarboxylates with aryl triflates at temperatures as low as 120 °C. Remarkably, polychlorinated and many heterocyclic arenecarboxylates are converted for the first time in high yields. FG=functional group.

  在比最知名的铜催化剂低50°C的条件下，催化银（I）/钯（II）系统可在低至120°C的温度下将芳族羧酸酯与芳基三氟甲磺酸酯进行脱羧交叉偶联。值得注意的是，多氯代芳烃羧酸酯和许多杂环芳烃羧酸酯首次以高收率转化。FG =功能组。
• Synthesis of Biaryls via Pd-Catalyzed Decarboxylative Coupling of Substituted Benzoic Acids with Phenylboronic Acids
  作者：Anwei Wang、Xiujian Li、Jidan Liu、Qingwen Gui、Xiang Chen、Ze Tan、Kai Xie

  DOI：10.1080/00397911.2013.804577

  日期：2014.1.17

  Abstract A Pd-catalyzed decarboxylative coupling of substituted benzoic acids with phenylboronic acid has been developed. Under the optimized conditions, a variety of substituted benzoic acids were found to undergo decarboxylative coupling with various phenylboronic acids to give the desired unsymmetrical biaryls in good yields. [Supplementary materials are available for this article. Go to the publisher's

  摘要 已经开发了 Pd 催化的取代苯甲酸与苯基硼酸的脱羧偶联反应。在优化的条件下，发现各种取代的苯甲酸与各种苯基硼酸进行脱羧偶联，以良好的产率得到所需的不对称联芳基化合物。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要