2-phenyl-1-(pyridin-2-yl)-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-phenyl-1-(pyridin-2-yl)-1H-indole
• 英文别名: 2-phenyl-1-(2-pyridyl)indole；2-Phenyl-1-pyridin-2-yl-1H-indole；2-phenyl-1-pyridin-2-ylindole
• 化学式: C₁₉H₁₄N₂
• 分子量: 270.334
• InChiKey: GNDVOWLVNORGSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenyl-1-(pyridin-2-yl)-1H-indole 在 三氟甲烷磺酸甲酯 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲醇 、 水 为溶剂， 反应 24.0h， 以89%的产率得到2-苯基吲哚
  参考文献：
  名称：

  通过Pd（II）催化的乙烯基叠氮化物苯胺环合反应合成2-Arylindoles

  摘要：

  在合成化学中，乙烯基叠氮化物被用作亲电子试剂，亲核试剂和自由基受体，并在制备N杂环系统中以快速，通用的合成子形式出现。在本文中，已经实现了经由Pd（II）催化的苯胺与乙烯基叠氮化物的环化反应制备2-芳基吲哚的新方法，其为通用的2-芳基吲哚提供了高效率和优异的区域选择性。

  DOI：

  10.1021/acs.joc.8b01618
• 作为产物：
  描述：

  2-苯胺基吡啶 在 disodium hydrogenphosphate 、 sodium amalgam 、 bis[(benzyldimethylamino)chloropalladium(II)] 、 sodium iodide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-phenyl-1-(pyridin-2-yl)-1H-indole
  参考文献：
  名称：

  Selective hetero- and carbo-cycle syntheses via masked cyclopalladated secondary amine and ketone functions

  摘要：

  The iodo-bridged or cationic cyclopalladated complexes Ib and Ic derived from N-phenyl-2-pyridylamine and 4b derived from phenyl-2-pyridylketone reacted with internal alkynes to yield five-membered heterocyclic 3 and carbocyclic products 6 with high chemoselectivity. The indoles 3b-3f, formed from Ib or Ic and disymmetric alkynes, were obtained regioselectively, suggesting that this reaction might be under both electronic and steric control. Analysis of the regiochemistry of this reaction has led us to propose a pathway involving a nucleophilic addition of the secondary amine function to an alkyne activated by eta(2)-coordination to palladium. The indenol derivatives 6, obtained as stable bis(O,N)-palladated chelates, result from the insertion of the alkyne into the Pd-C bond of 4b followed by attack of the palladated vinyl carbon atom on the electrophilic carbonyl function. In so far as their reactivities towards alkynes are concerned, Ib and Ic behave as masked cyclopalladated secondary amine functions and 4b as masked cyclopalladated ketone functions.

  DOI：

  10.1016/0022-328x(94)88054-9

文献信息

• Rhodium-catalyzed C–H functionalization with N-acylsaccharins
  作者：Hongxiang Wu、Tingting Liu、Ming Cui、Yue Li、Junsheng Jian、Hui Wang、Zhuo Zeng

  DOI：10.1039/c6ob02526a

  日期：——

  A rhodium-catalyzed C–H functionalization with activated amides by decarbonylation has been developed. Notably, this is the first C–H arylation employing N-acylsaccharins as coupling partners to give biaryls in good to excellent yields. The highlight of the work is the high tolerance of functional groups such as formyl, ester, and vinyl and the use of a removable directing group.

  通过脱羰作用，用活化的酰胺对铑催化的CH官能团进行了开发。值得注意的是，这是第一个使用N-酰基糖精作为偶联伙伴的C–H芳基化反应，可以产生高至优异收率的联芳基。这项工作的重点是对甲酰基，酯和乙烯基等官能团的高度耐受性，以及可移动的导向基团的使用。
• Iridium(III)-Catalyzed Tandem Annulation of Pyridine-Substituted Anilines and α-Cl Ketones for Obtaining 2-Arylindoles
  作者：Xin-Feng Cui、Xin Qiao、He-Song Wang、Guo-Sheng Huang

  DOI：10.1021/acs.joc.0c01619

  日期：2020.11.6

  readily available N-(2-pyridyl)anilines and commercially available α-Cl ketones through iridium-catalyzed C–H activation and cyclization is reported here. As a complementary approach to the conventional strategies for indole synthesis, the transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds with good to excellent yields under mild conditions, providing

  此处报道了一种简便易行的方案，可通过铱催化的C–H活化和环化作用，从易于获得的N-（2-吡啶基）苯胺和市售的α-Cl酮合成2-芳基吲哚化合物。作为吲哚合成常规策略的一种补充方法，该转化反应显示出强大的反应活性，可以耐受大量的官能团，并且在温和的条件下以良好或优异的产率进行合成，为获得结构多样且有价值的吲哚支架提供了直接的方法。此外，反应可以容易地放大至克级。
• Rhodium-catalyzed regioselective direct C–H arylation of indoles with aryl boronic acids
  作者：Liang Wang、Xing Qu、Zhan Li、Wang-Ming Peng

  DOI：10.1016/j.tetlet.2015.04.015

  日期：2015.6

  A highly efficient Rh(III)-catalyzed direct C–H arylation of indoles with aryl boronic acids under mild conditions has been developed. The methodology features wide substrate scope and excellent functional group compatibility (34 examples, up to 99% yield). The arylated products can also be conveniently transformed into biologically active polycyclic indole derivatives.

  在温和的条件下，已开发出高效的Rh（III）催化的吲哚与芳基硼酸的直接C–H芳基化反应。该方法具有广泛的底物范围和出色的官能团相容性（34个实例，产率高达99％）。芳基化产物也可以方便地转化为具有生物活性的多环吲哚衍生物。
• Ruthenium-Catalyzed Direct C–H Bond Arylations of Heteroarenes
  作者：Lutz Ackermann、Alexander V. Lygin

  DOI：10.1021/ol2010648

  日期：2011.7.1

  Ruthenium-catalyzed C–H bond arylations of indoles, thiophenes, and pyrroles were accomplished in a highly chemo- and site-selective manner through the use of removable directing groups.

  钌催化的吲哚，噻吩和吡咯的C H键芳基化是通过使用可移动的导向基团以高度化学和位点选择性的方式完成的。
• Cobalt(II)-Catalyzed Oxidative C–H Arylation of Indoles and Boronic Acids
  作者：Xinju Zhu、Jian-Hang Su、Cong Du、Zheng-Long Wang、Chang-Jiu Ren、Jun-Long Niu、Mao-Ping Song

  DOI：10.1021/acs.orglett.6b03746

  日期：2017.2.3

  Co(II)-catalyzed C–H C2 selective arylation of indoles with boronic acids through monodentate chelation assistance has been achieved for the first time. The unique features of this methodology include mild reaction conditions, highly C2 regioselectivity, and employment of a Grignard reagent-free catalytic system. A wide range of substrates, including unreactive arenes, are well tolerated, which enables

  首次通过单齿螯合助剂实现了Co（II）催化的吲哚与硼酸的C–H C2选择性芳基化。该方法的独特之处包括温和的反应条件，高度的C2区域选择性以及采用格氏试剂无催化体系。包括非反应性芳烃在内的各种基材均具有良好的耐受性，从而可以高效地构建偶联产物。该新策略提供了使用廉价的钴催化剂构建联芳基的另一种通用方法。