2-(2,6-dimethylphenyl)benzofuran

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(2,6-dimethylphenyl)benzofuran
• 英文别名: 2-(2,6-Dimethylphenyl)-1-benzofuran；2-(2,6-dimethylphenyl)-1-benzofuran
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: TYLJUVUAAGCKLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3-苯并呋喃 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 sodium carbonate 、 三(邻甲基苯基)磷 、 4,4'-二叔丁基-2,2'-二吡啶 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 生成 2-(2,6-dimethylphenyl)benzofuran
  参考文献：
  名称：

  A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates

  摘要：

  A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.

  DOI：

  10.1021/ol301570t

文献信息

• Microwave-Assisted Suzuki Coupling Reactions with an Encapsulated Palladium Catalyst for Batch and Continuous-Flow Transformations
  作者：Ian R. Baxendale、Charlotte M. Griffiths-Jones、Steven V. Ley、Geoffrey K. Tranmer

  DOI：10.1002/chem.200501400

  日期：2006.5.24

  This article describes the design, optimisation and development of a Suzuki cross-coupling protocol mediated by an efficient palladium-encapsulated catalyst (Pd EnCat) under microwave irradiation. The methodology has been used in both batch mode for classical library preparation and in continuous-flow applications furnishing multigram quantities of material. Described is a method that uses direct focused

  本文介绍了在微波辐射下由高效钯封装的催化剂（Pd EnCat）介导的Suzuki交叉偶联方案的设计，优化和开发。该方法已在批处理模式下用于经典文库制备，并已在连续流应用中使用，以提供数克的材料。描述了一种在施加外部冷却源的同时使用直接聚焦微波加热的方法。这使得可以在整个反应期间保持低于正常的总体温度，从而导致反应产物的总产率和纯度的显着提高。关于固定催化剂体系的延长寿命和增强的反应性，讨论了该新颖的加热方案的其他方面。
• Cross-Coupling Reactions of Aromatic and Heteroaromatic Silanolates with Aromatic and Heteroaromatic Halides
  作者：Scott E. Denmark、Russell C. Smith、Wen-Tau T. Chang、Joseck M. Muhuhi

  DOI：10.1021/ja8091449

  日期：2009.3.4

  use of bis(tri-tert-butylphosphine)palladium. Under the optimized conditions, electron-rich, electron-poor, and sterically hindered arylsilanolates afford cross-coupling products in good yields. Many functional groups are compatible with the coupling conditions such as esters, ketones, acetals, ethers, silyl ethers, and dimethylamino groups. Two particularly challenging substrates, (2-benzofuranyl)dimethylsilanolate

  大量芳基和杂芳基硅烷醇的碱金属盐（钾和钠）在温和条件下与多种芳香族溴化物和氯化物进行有效交叉偶联，形成多取代联芳基化合物。这些偶联反应成功的关键特征及其相当大的范围是使用双（三叔丁基膦）钯。在优化条件下，富电子、缺电子和空间位阻芳基硅烷醇化物以良好的产率提供交叉偶联产物。许多官能团与偶联条件相容，例如酯、酮、缩醛、醚、甲硅烷基醚和二甲氨基。两种特别具有挑战性的底物，(2-苯并呋喃基)二甲基硅烷醇盐和 (2, 以钠盐形式制备的 6-二氯苯基）二甲基硅烷醇化物在偶联反应中表现出优异的活性，在前一种情况下也与芳族氯化物。还描述了有效合成范围广泛的芳族硅烷醇的一般方法。
• A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates
  作者：Daniel W. Robbins、John F. Hartwig

  DOI：10.1021/ol301570t

  日期：2012.8.17

  A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.