2-allyl-1-(pyrimidin-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-allyl-1-(pyrimidin-2-yl)-1H-indole
• 英文别名: 2-Prop-2-enyl-1-pyrimidin-2-ylindole；2-prop-2-enyl-1-pyrimidin-2-ylindole
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: CBJWJTAROCJBPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(嘧啶-2-基)-1H-吲哚 、 乙酸烯丙酯 在 silver hexafluoroantimonate 、 [Cp*Co(CO)I₂] 、 potassium acetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以96%的产率得到2-allyl-1-(pyrimidin-2-yl)-1H-indole
  参考文献：
  名称：

  Cobalt(III)-Catalyzed Allylation with Allyl Acetates by C–H/C–O Cleavage

  摘要：

  Versatile cobalt-catalyzed C-H allylations on arenes, indoles, and pyrroles were accomplished with allyl acetates. The C-H/C-O functionalization process was characterized by a broad substrate scope as well as an excellent functional-group tolerance and was shown to occur by initial C-H cobaltation.

  DOI：

  10.1055/s-0034-1379927

文献信息

• <scp>Cobalt‐Catalyzed</scp> C—H Allylation of Arenes with Allylic Amines
  作者：Rui Yan、Hang Yu、Zhong‐Xia Wang

  DOI：10.1002/cjoc.202000680

  日期：2021.5

  catalyzes pyridyl‐directed C—H allylation of arenes with allylic amines in the presence of AgOAc and CF3COOAg. The reaction features ortho‐position monoallylation of 2‐pyridylarenes, giving the allylated arenes in moderate to high yields. A range of functional groups including OMe, Me, Ph, F, Cl, Br, CF3, C(O)Me, COOEt, and COOH groups are tolerated. Pyrimidyl‐directed C—H allylation of arenes were also performed

  在AgOAc和CF 3 COOAg存在下，[Cp * Co（CO）I 2 ]有效催化芳烃与吡啶基定向的CH烯丙基化。该反应具有2-吡啶基芳烃的邻位单烯丙基化的特征，从而使烯丙基化的芳烃具有中等至高收率。允许的官能团范围包括OMe，Me，Ph，F，Cl，Br，CF 3，C（O）Me，COOEt和COOH。在相同条件下还进行了芳基的嘧啶基C H烯丙基化反应。2-苯基嘧啶，2-（4-甲氧基苯基）嘧啶和2-（3-氟苯基）嘧啶的反应导致邻位单烯丙基化和双烯丙基化产物的混合物。其他2-（取代的芳基）嘧啶的反应导致邻位位置单烯丙基化产物。
• Mild Rhodium(III)-Catalyzed Direct CH Allylation of Arenes with Allyl Carbonates
  作者：Honggen Wang、Nils Schröder、Frank Glorius

  DOI：10.1002/anie.201301165

  日期：2013.5.10

  All(yl) possible! A rhodium(III)‐catalyzed intermolecular direct CH allylation reaction utilizing readily accessible allyl carbonates was developed. This method allows the allylation of electron‐neutral arenes, providing complete γ‐selectivity, high isomeric ratio, good substrate scope, and excellent functional group compatibility.

  所有（yl）可能！开发了一种铑（III）催化的分子间直接CH烯丙基化反应，该反应使用易于获得的碳酸烯丙酯。该方法允许电子中性芳烃的烯丙基化，提供完全的γ选择性，高异构体比，良好的底物范围和出色的官能团相容性。
• Co(III)-Catalyzed C–H Activation/Formal S_N-Type Reactions: Selective and Efficient Cyanation, Halogenation, and Allylation
  作者：Da-Gang Yu、Tobias Gensch、Francisco de Azambuja、Suhelen Vásquez-Céspedes、Frank Glorius

  DOI：10.1021/ja511011m

  日期：2014.12.24

  The first cobalt-catalyzed cyanation, halogenation, and allylation via C-H activation have been realized. These formal SN-type reactions generate valuable (hetero)aryl/alkenyl nitriles, iodides, and bromides as well as allylated indoles using a bench-stable Co(III) catalyst. High regio- and mono-selectivity were achieved for these reactions. Additionally, allylation proceeded efficiently with a turnover

  首次实现了钴催化的氰化、卤化和通过 CH 活化的烯丙基化。这些正式的 SN 型反应使用长期稳定的 Co(III) 催化剂生成有价值的（杂）芳基/烯基腈、碘化物和溴化物以及烯丙基化吲哚。这些反应实现了高区域选择性和单选择性。此外，烯丙基化在室温下以 2200 的周转数有效进行，这对于这种 Co(III) 催化剂来说是前所未有的。烯基底物和酰胺首次成功用于 Cp*Co(III) 催化的 CH 活化。
• Dehydrative Direct CH Allylation with Allylic Alcohols under [Cp*Co ^III ] Catalysis
  作者：Yudai Suzuki、Bo Sun、Ken Sakata、Tatsuhiko Yoshino、Shigeki Matsunaga、Motomu Kanai

  DOI：10.1002/anie.201503704

  日期：2015.8.17

  dehydrative CH allylation with non‐activated allyl alcohols, thus giving C2‐allylated indoles, pyrrole, and phenyl‐pyrazole in good yields, while analogous [Cp*RhIII] catalysts were not effective. The high γ‐selectivity and C2‐selectivity indicated that the reaction proceeded by directing‐group‐assisted CH metalation. DFT calculations suggested that the γ‐selective substitution reaction proceeded by CH metalation

  证明了[Cp * Co III ]相对于[Cp * Rh III ]的独特反应性。阳离子型[Cp * Co III ]催化剂可促进未活化的烯丙醇直接脱水使CH烯丙基化，从而获得高收率的C2烯丙基化的吲哚，吡咯和苯基吡唑，而类似的[Cp * Rh III ]催化剂是没有效果。较高的γ选择性和C2选择性表明该反应是通过引导基团辅助的CH金属化而进行的。DFT计算表明，通过CH金属化和插入CC双键进行了γ-选择性取代反应，随后消除了β-氢氧根。[Cp * CoIII ]催化剂比β-氢化物的消除更有利于β-氢氧化物的消除。
• Cobalt(III)-Catalyzed Directed C–H Allylation
  作者：Tobias Gensch、Suhelen Vásquez-Céspedes、Da-Gang Yu、Frank Glorius

  DOI：10.1021/acs.orglett.5b01701

  日期：2015.8.7

  The cobalt(III)-catalyzed allylation was developed for amide-directed C-H activation of arenes, heteroarenes, and olefins. A variety of allyl sources can be employed to introduce this useful functional group.