6-methyl-10-phenylbenzo[h]quinoline | 1415320-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-methyl-10-phenylbenzo[h]quinoline
• CAS: 1415320-72-7
• 化学式: C₂₀H₁₅N
• 分子量: 269.346
• InChiKey: DOIJHCMQMSFOQU-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  (6-methylbenzo[h]quinolin-10-yl)methanol 、 苯硼酸 在 Wilkinson's catalyst 、 copper(l) chloride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 15.0h， 以87%的产率得到6-methyl-10-phenylbenzo[h]quinoline
  参考文献：
  名称：

  Efficient Approach To Construct Unsymmetrical Biaryls through Oxidative Coupling Reactions of Aromatic Primary Alcohols and Arylboronic Acids with a Rhodium Catalyst

  摘要：

  Unsymmetrical biaryls were synthesized by oxidative coupling reactions, between aromatic primary alcohols and arylboronic acids through the C-C bond cleavage of the primary alcohols chelated With a rhodium catalyst. The desired unsymmetrical biaryl products were obtained in good to excellent yields under the optimized reaction conditions. A wide variety of functionalities are compatible with the reaction under the optimized conditions. This new coupling strategy provides a favorable method to construct valuable biaryl compounds from aromatic primary alcohols which are cheap; environmentally friendly, and easily accessible substrates.

  DOI：

  10.1021/acs.organomet.6b00238

文献信息

• Rhodium-Catalyzed Cross-Coupling Reactions of Carboxylate and Organoboron Compounds via Chelation-Assisted C–C Bond Activation
  作者：Jingjing Wang、Bowen Liu、Haitao Zhao、Jianhui Wang

  DOI：10.1021/om300994j

  日期：2012.12.24

  A new rhodium-catalyzed decarbonylated coupling reaction of ethyl benzo[h]quinoline-10-carboxylate and organoboron compounds that occurs through chelation-assisted sp2 C–COOEt bond activation was described. In this system CuCl played a very important role, and a five-membered rhodacycle was also involved as a key intermediate. Various functionalities were compatible in the reaction, and the desired

  描述了一种新的铑催化的苯并[ h ]喹啉-10-羧酸乙酯与有机硼化合物的脱羰偶联反应，该反应通过螯合辅助的sp 2 C-COOEt键活化而发生。在该系统中，CuCl发挥了非常重要的作用，并且五元罗丹环也作为关键中间体参与其中。在反应中各种官能团是相容的，并且以良好至优异的产率获得了所需的产物。还已经使用Rh（I）模型催化剂对该反应机理进行了DFT计算。
• Rhodium-catalyzed decarbonylation cross-coupling reactions of aromatic aldehydes and arylboronic acids via C C bond activation directed by a guide group chelation
  作者：Xiaobo Yu、Guanchen Liu、Shudong Geng

  DOI：10.1016/j.inoche.2020.108065

  日期：2020.9

  Abstract A rhodium-catalyzed decarbonylative cross-coupling reaction of benzoquinoline-10-carbaldehydes with arylboronic acids through chelation-assisted sp2 C−CHO bond activation has been developed. A variety of functional groups substituted phenylboronic acids or benzoquinoline-10-carbaldehydes are compatible with the reaction under the optimized reaction conditions, the corresponding 10-phenylbenzo[h]quinoline

  摘要 已经开发了铑催化的苯并喹啉-10-甲醛与芳基硼酸通过螯合辅助 sp2 C-CHO 键活化的脱羰交叉偶联反应。在优化的反应条件下，多种官能团取代的苯基硼酸或苯并喹啉-10-甲醛与反应相容，相应的10-苯基苯并[h]喹啉衍生物以中等至良好的收率获得。该方法为通过铑催化的 sp2 C-CHO 键活化合成 N-杂环联芳基化合物提供了一种有用的策略。