2-(2,4-difluorophenyl)-benzooxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,4-difluorophenyl)-benzooxazole
• 英文别名: 2-(2,4-difluorophenyl)benzoxazole；2-(2,4-Difluorophenyl)-1,3-benzoxazole
• 化学式: C₁₃H₇F₂NO
• 分子量: 231.201
• InChiKey: CPKISXNPGFWPMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,4-difluorophenyl)-benzooxazole 、 [osmium(II)dichloride(dicarbonyl)()(triphenylphosphane)2] 生成 Os[P(C₆H₅)₃]₂(CO)(2,4-F₂-pbo)Cl
  参考文献：
  名称：

  杂配环金属化二价锇Os[P(C6H5)3]2(CO)(N∩C−)Cl配合物的合成与表征

  摘要：

  摘要 简单的合成过程，Os[P(C 6 H 5 ) 3 ] 2 (CO) 2 Cl 2 与 2-苯基吡啶（或其他类似的 N∩CH 螯合配体）在沸腾的 2-(2-乙氧基乙氧基)乙醇溶液中的反应导致 Os[P(C 6 H 5 ) 3 ] 2 (CO)(N∩C - )Cl 配合物。所得物质的结构已通过 31 P NMR 和 FT-IR 技术以及元素分析数据阐明。新合成配合物的紫外-可见吸收和发射特性揭示了其最低单线态和三线态激发态的 MLCT 特性。

  DOI：

  10.1016/j.inoche.2013.09.022
• 作为产物：
  描述：

  苯并恶唑 、 1-溴-2,4-二氟苯 在 PdCl(C₃H₅)(dppb) caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以82%的产率得到2-(2,4-difluorophenyl)-benzooxazole
  参考文献：
  名称：

  Direct arylation of oxazole and benzoxazole with aryl or heteroaryl halides using a palladium–diphosphine catalyst

  摘要：

  Through the use of PdCl(dppb)(C3H5) as a catalyst, a range of aryl bromides and chlorides undergoes coupling via C-H bond activation/flunctionalization reaction with oxazole or benzoxazole in good yields. This air-stable catalyst can be used at low loadings with several substrates. Surprisingly, better results in terms of substrate/catalyst ratio were obtained in several cases using electron-excessive aryl bromides than with the electron-deficient ones. This seems to be mainly due to the relatively low thermal stability of some of the 2-arylbenzoxazoles formed with electron -deficient aryl halides. With these substrates, in order to obtain higher yields of product, the reactions had to be performed at a lower temperature (100-120 degrees C) using a larger amount of catalyst. On the other hand, in the presence of the most stable products, the reactions were performed at 150 degrees C using as little as 0.2 mol% catalyst. Arylation of benzoxazole with heteroaryl bromides also gave the coupling products in moderate to high yields using 0.2-5 mol% catalyst. With this catalyst, electron-deficient aryl chloride such as 4-chlorobenzonitrile, 4-chloroacetophenone or 2-chloronitrobenzene have also been used successfully. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.10.028

文献信息

• Nickel-Catalyzed Decarboxylative Arylation of Heteroarenes through sp²C-H Functionalization
  作者：Ke Yang、Peng Wang、Cheng Zhang、Adnan A. Kadi、Hoong-Kun Fun、Yan Zhang、Hongjian Lu

  DOI：10.1002/ejoc.201403234

  日期：2014.12

  The direct decarboxylative arylation of hetereoarenes with benzoic acids through a nickel-catalyzed sp2 C–H functionalization process was developed. This process provides the first examples of decarboxylative cross-coupling reactions with aromatic acids through nickel catalysis and tolerates a variety of functional groups. Moreover, this method provides efficient access to 2-aryl-substituted azoles

  通过镍催化的 sp2 C-H 功能化过程，杂芳烃与苯甲酸直接脱羧芳基化。该过程提供了通过镍催化与芳香酸进行脱羧交叉偶联反应的第一个例子，并且可以耐受各种官能团。此外，该方法提供了对 2-芳基取代唑的有效获取，2-芳基取代唑是天然产物、药用化合物和功能材料中的重要结构单元。
• A one-pot, two-step microwave-assisted synthesis of highly functionalized benzoxazoles using solid-supported reagents (SSRs)
  作者：Marco Radi、Sara Saletti、Maurizio Botta

  DOI：10.1016/j.tetlet.2008.05.059

  日期：2008.7

  A one-pot, two-step protocol for the microwave-assisted solid-phase synthesis of substituted benzoxazoles has been developed starting from different polymer-bound esters we previously designed as solid-supported reagents (SSRs) for the acylation of amines, alcohols and phenols. The combination of a parallel synthesizer and a microwave reactor allowed to quickly prepare a collection of substituted benzoxaxoles

  已开发了一锅，两步的微波辅助固相合成取代苯并恶唑的规程，它是从我们先前设计为胺，醇和胺的酰化的固载试剂（SSR）的不同聚合物结合的酯开始的。酚类。平行合成器和微波反应器的组合可以快速制备高纯度和令人满意的收率的取代苯并恶唑的集合。该协议适用于自动化，可用于药物发现程序中组合库的制备。
• Palladium-catalyzed non-directed C–H bond arylation of difluorobenzenes and dichlorobenzenes bearing benzoxazole or benzothiazole
  作者：Fatma Abdellaoui、Hamed Ben Ammar、Jean-François Soulé、Henri Doucet

  DOI：10.1016/j.catcom.2015.07.025

  日期：2015.11

  We report, herein, on palladium-catalyzed direct arylation of difluorobenzenes and dichlorobenzenes bearing benzoxazole or benzothiazole moieties, which don't act as directing groups. With moderate electron-withdrawing substituents on the aryl bromides as coupling partners, the reaction proceeds nicely using phosphine-free PdCl2 catalyst, and potassium pivalate/dimethylacetamide (PivOK/DMA) as catalytic

  在本文中，我们报道了钯催化带有苯并恶唑或苯并噻唑部分的二氟苯和二氯苯的直接芳基化，它们不充当引导基团。在芳基溴化物上具有适度的吸电子取代基作为偶联伙伴的情况下，使用无膦的PdCl 2催化剂和新戊酸钾/二甲基乙酰胺钾（PivOK / DMA）作为催化体系，反应可以顺利进行。该反应是区域选择性的，发生在氟或氯原子受阻较小的邻位。
• Polymers with heterocyclic side groups
  申请人：MAXDEM INCORPORATED

  公开号：EP0773248A1

  公开（公告）日：1997-05-14

  A new class of polymers include repeating units comprising one or more arylene units substituted with heterocyclic side groups. The heterocyclic substituted arylene repeat units have the general structural formula: wherein Het is a heterocyclic group, R is an optional substituent, x is 1 or 2, and y is less than or equal to 4-x.

  一类新型聚合物包括由一个或多个被杂环侧基取代的芳烯单元组成的重复单元。杂环取代的芳烯重复单元具有一般结构式： 其中 Het 是杂环基团，R 是任选取代基，x 是 1 或 2，y 小于或等于 4-x。
• Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[<i>d</i>]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects
  作者：Shuang Huang、Xi Hong、He-Zhen Cui、Bing Zhan、Zhi-Ming Li、Xiu-Feng Hou

  DOI：10.1021/acs.organomet.0c00464

  日期：2020.10.12

  Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significant increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogues (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both Cl and H-2 source. Substrates, including aromatic amines, ketones, and nitro compounds with various functional groups, can be well-tolerated. Mechanistic studies and DFT calculation highlight the significance of bimetallic centers cooperativity.