2,3-diphenyl-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: 2,3-diphenyl-1-(pyridin-2-yl)-1H-indole
• 英文别名: 2,3-Diphenyl-1-pyridin-2-ylindole；2,3-diphenyl-1-pyridin-2-ylindole
• 化学式: C₂₅H₁₈N₂
• 分子量: 346.431
• InChiKey: ILGBZHIDENFUBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• 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

• 作为产物：
  描述：

  2-溴吡啶 在 双(乙腈)氯化钯(II) 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 copper dichloride 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2,3-diphenyl-1-(pyridin-2-yl)-1H-indole
  参考文献：
  名称：

  Pd（II）催化氧化偶联反应合成N-（2-吡啶基）吲哚

  摘要：

  容易获得的Pd（II）氯化物催化剂可以催化之间的选择性的和有效的氧化偶合ñ -芳基-2-氨基吡啶和内部炔烃，得到ñ - （2-吡啶基）吲哚。该过程涉及N-芳基-2-氨基吡啶的邻位CH活化，并且CuCl 2被用作氧化剂。与我们先前报道的Rh（III）催化的这类产物的合成相比，该方法在炔烃和成本效益较高的Pd（II）催化剂方面具有优势。分子氧可以用作末端氧化剂。

  DOI：

  10.1021/jo1025546

文献信息

• Nickel-catalyzed alkyne annulation by anilines: versatile indole synthesis by C–H/N–H functionalization
  作者：Weifeng Song、Lutz Ackermann

  DOI：10.1039/c3cc43915a

  日期：——

  Versatile nickel catalysts enabled the step-economical synthesis of decorated indoles through alkyne annulations with anilines bearing removable directing groups. The C–H/N–H activation strategy efficiently occurred in the absence of any metal oxidants and with excellent selectivities.

  多功能镍催化剂实现了通过带有可移除导向基团的苯胺与炔烃环化反应的经济型合成修饰吲哚。C–H/N–H活化策略在没有金属氧化剂的情况下高效进行，并具有极佳的选择性。
• Synthesis of 2-Arylindoles through Pd(II)-Catalyzed Cyclization of Anilines with Vinyl Azides
  作者：Lianghua Jie、Lianhui Wang、Dan Xiong、Zi Yang、Di Zhao、Xiuling Cui

  DOI：10.1021/acs.joc.8b01618

  日期：2018.9.21

  featured as electrophiles, nucleophiles, and radical acceptors in synthetic chemistry and have emerged as rapid and versatile synthons in the preparation of N-heterocyclic systems. Herein, a novel approach to 2-arylindoles via Pd(II)-catalyzed cyclization reaction of anilines with vinyl azides has been achieved, which furnishes the versatile 2-arylindoles with high efficieny and excellent regioselectivity

  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。
• Nanocrystalline magnesium oxide-stabilized palladium(0): an efficient and reusable catalyst for synthesis of N-(2-pyridyl)indoles
  作者：Police Vishnuvardhan Reddy、Manne Annapurna、Pottabathula Srinivas、Pravin R. Likhar、Mannepalli Lakshmi Kantam

  DOI：10.1039/c5nj00074b

  日期：——

  A selective and efficient catalytic process has been developed for the oxidative coupling between N-aryl-2-aminopyridines and alkynes using a nanocrystalline magnesium oxide (NAP–MgO)-supported palladium nanoparticle [NAP–Mg–Pd(0)] catalyst and CuCl2 as an oxidant. The process involves the ortho C–H activation of N-aryl-2-aminopyridines to give N-pyridyl indoles in excellent yields and the true heterogeneity

  已经开发出一种选择性和有效的催化方法，以使用纳米晶氧化镁（NAP–MgO）负载的钯纳米颗粒[NAP–Mg–Pd（0）]催化剂和CuCl催化N-芳基-2-氨基吡啶和炔烃之间的氧化偶联。2作为氧化剂。该过程涉及N-芳基-2-氨基吡啶的邻位C–H活化，从而以优异的收率得到N-吡啶基吲哚，并且通过研究四个循环的可回收性和可重复使用性而证实了催化剂的真正非均相性，而不会显着降低催化活性。 。
• Rh(III)-Catalyzed Oxidative Coupling of <i>N</i>-Aryl-2-aminopyridine with Alkynes and Alkenes
  作者：Jinlei Chen、Guoyong Song、Cheng-Ling Pan、Xingwei Li

  DOI：10.1021/ol1022596

  日期：2010.12.3

  [RhCp*Cl-2](2) (1-2 mol %) can catalyze the oxidative coupling of N-aryl-2-aminopyridines with alkynes and arylates to give N-(2-pyridyl)indoles and N-(2-pyridyl)quinolones, respectively, using Cu(OAc)(2) as an oxidant. Coupling with styrenes gave mono- and/or disubstituted olefination products.
• Selective hetero- and carbo-cycle syntheses via masked cyclopalladated secondary amine and ketone functions
  作者：F. Maassarani、M. Pfeffer、J. Spencer、E. Wehman

  DOI：10.1016/0022-328x(94)88054-9

  日期：1994.2

  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.