4-ethylbenzenediazonium tetrafluoroborate | 52436-73-4

• 英文名称: 4-ethylbenzenediazonium tetrafluoroborate
• 英文别名: 4-ethylphenyldiazonium tetrafluoroborate
• CAS: 52436-73-4
• 化学式: BF₄*C₈H₉N₂
• 分子量: 219.977
• InChiKey: XUAKYHVZQMWKOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  4-ethylbenzenediazonium tetrafluoroborate 在 ferrous(II) sulfate heptahydrate 、 双氧水 、 silver nitrate 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 2.67h， 生成 5-bromo-3-(4-ethylphenyl)-2-(2,2,2-trifluoroethyl)-1H-indole
  参考文献：
  名称：

  通过烯烃官能化的级联多组分合成吲哚，吡唑和吡嗪酮

  摘要：

  用于吲哚合成的多组分反应的开发是需要的，并且几乎没有被探索。本研究描述了吲哚合成的新型多组分，级联方法的发展。通过使用已建立的直接和区域选择性方法，可以从简单的试剂（例如未官能化的烯烃，重氮盐和三氟甲磺酸钠）中获得各种取代的吲哚衍生物。该方法是基于烯烃的自由基三氟甲基化作为费歇尔吲哚合成的入口。除了吲哚合成外，还描述了多组分级联反应在吡唑和哒嗪酮合成中的应用。

  DOI：

  10.1002/anie.201406464
• 作为产物：
  描述：

  4-乙基苯胺 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以62%的产率得到4-ethylbenzenediazonium tetrafluoroborate
  参考文献：
  名称：

  Antivitamins B12: Synthesis and application as inhibitory ligand of the B12-tailoring enzyme CblC

  摘要：

  DOI：

  10.1016/bs.mie.2021.12.016

文献信息

• Copper(I)-promoted trifluoromethylthiolation of arenediazonium salts with AgSCF3
  作者：Changge Zheng、Yang Liu、Jianquan Hong、Shuai Huang、Wei Zhang、Yupeng Yang、Ge Fang

  DOI：10.1016/j.tetlet.2019.04.018

  日期：2019.5

  An efficient method for trifluoromethylthiolation of arenediazonium salts has been developed in mild conditions with a stable and convenient AgSCF3. It provides a straightforward and convenient way for the synthesis of trifluoromethylthiolated compound from diazonium salts in moderate to good yields.

  在稳定和方便的AgSCF 3的温和条件下，开发了一种有效的方法用于芳构氮杂鎓盐的三氟甲基硫醇化。它为重氮盐以中等到良好的收率合成三氟甲基硫醇化化合物提供了一种直接简便的方法。
• Merging [2+2] Cycloaddition with Radical 1,4-Addition: Metal-Free Access to Functionalized Cyclobuta[<i>a</i> ]naphthalen-4-ols
  作者：Feng Liu、Jia-Yin Wang、Peng Zhou、Guigen Li、Wen-Juan Hao、Shu-Jiang Tu、Bo Jiang

  DOI：10.1002/anie.201707615

  日期：2017.12.4

  Just a DAB: A new metal-free [2+2] cycloaddition/S-centered radical induced 1,4-addition sequence of benzene-linked allene-ynes has been established by treatment with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) under convenient reaction conditions, thus providing practical access to functionalized cyclobuta[a]naphthalen-4-ols of chemical and biomedical importance. DABCO=1,4-diazabicyclo[2

  只是一个DAB：通过四氟硼酸芳基重氮盐和DABCO-bis（二氧化硫）处理，建立了一种新的无金属[2 + 2]环加成/ S中心自由基诱导的苯连接的丙二烯炔的1,4-加成序列。方便的反应条件下，从而提供官能cyclobuta实际访问[一个]萘-4-醇的化学和生物医学重要性。DABCO ＝ 1，4-二氮杂双环[2.2.2]辛烷。
• The synthesis and structural characterisation of some azo-containing phosphine chalcogenides and comparison to non-phosphorus-containing analogues
  作者：Mark J. Alder、Vanessa M. Bates、Wendy I. Cross、Kevin R. Flower、Robin G. Pritchard

  DOI：10.1039/b104918f

  日期：2001.10.11

  p-HO-Ph(Ph2)P(E) (E = S, 1b, Se, 1c) reacts with the diazonium salts [4-R-PhNN][BF4] (R = H, Me, Et, iPr, tBu, NMe2, NO2) to afford the new compounds [1-HO-2-(4-R-PhNN)-4-Ph2P(E)C6H3] (E = S, R = H, 2a; Me, 2b; Et, 2c; iPr, 2d; tBu, 2e; NMe2, 2f; NO2, 2g; E = Se, R = H, 2h; Me, 2i) in acceptable yield. Similarly m-HO-Ph(Ph2)P(S) 3 reacts with two molar equivalents of the diazonium salts [4-R-PhNN][BF4] (R = H, Me, NMe2, NO2) to give the new compounds 1-HO-2,4-(4-R-PhNN)-3-Ph2P(S)-C6H24a–d (R = H, 4a; Me, 4b; NMe2, 4c; NO2, 4d). All of the new compounds have been characterised by elemental analysis, 1H, 31P-1H}, 13C-1H}-NMR spectroscopy and in selected cases UV–visible spectroscopy. The selectivity in the substitution reactions of 3 with the diazonium salts is influenced not only by the steric bulk of the Ph2PS moiety but by the ortho-effect too. These data have been compared to those obtained from analogous coupling reactions between m-cresol and one and two molar equivalents of [4-Me-PhNN][BF4] which afford 1-HO-3-CH3-4-(4-Me-PhNN)C6H35 and 1-HO-3-CH3-2,4-(4-Me-PhNN)C6H26 respectively. The compounds 2b·0.55CH2Cl2·0.2C6H14, 4b·CH2Cl2, 5 and 6b have been further characterised by X-ray crystallography.

  p-HO-Ph(Ph2)P(E) (E = S, 1b, Se, 1c)与重氮盐[4-R-PhNN][BF4] (R = H, Me, Et, iPr, tBu, NMe2, NO2)反应，得到新化合物[1-HO-2-(4-R-PhNN)-4-Ph2P(E)C6H3] (E = S, R = H, 2a; Me, 2b; Et, 2c; iPr, 2d; tBu, 2e; NMe2, 2f; , 2g; E = Se, R = H, 2h; Me, 2i)，产率良好。同样，m-HO-Ph(Ph2)P(S) 3与两摩尔重氮盐[4-R-PhNN][BF4] (R = H, Me, NMe2, )反应，生成新化合物1-HO-2,4-(4-R-PhNN)-3-Ph2P(S)-C6H24a–d (R = H, 4a; Me, 4b; NMe2, 4c; , 4d)。所有新化合物均通过元素分析、1H、31P-1H}和13C-1H}-NMR光谱以及在某些情况下的紫外-可见光谱进行了表征。3与重氮盐的取代反应选择性不仅受Ph2PS部分的立体体积影响，还受到邻位效应的影响。这些数据与m-克雷索尔与一摩尔和两摩尔重氮盐[4-Me-PhNN][BF4]的类似偶联反应得到的结果进行了比较，分别得到1-HO-3-CH3-4-(4-Me-PhNN)C6H35和1-HO-3- -2,4-(4-Me-PhNN)C6H26。化合物2b·0.55 ·0.2C6H14、4b·CH2Cl2、5和6b则通过X射线晶体学进一步表征。
• Palladium-Catalyzed Ligand-Free Decarboxylative Coupling of α- Oxocarboxylic Acid with Aryl Diazonium Tetrafluoroborate: An Access to Unsymmetrical Diaryl Ketones
  作者：Subir Panja、Pintu Maity、Brindaban C. Ranu

  DOI：10.1021/acs.joc.8b01922

  日期：2018.10.19

  Diaryl ketones are of much importance in organic synthesis as versatile intermediates and in industry for their useful properties. A mild and efficient palladium-catalyzed traditional ligand-free decarboxylative coupling of aryl α-keto carboxylic acid with aryl diazonium fluoroborate has been developed. A series of unsymmetrical diaryl ketones has been synthesized in moderate to good yields using this

  二芳基酮作为有用的中间体在有机合成中和工业上都非常重要。已开发出温和而有效的芳族α-酮基羧酸与芳基重氮氟硼酸酯的钯催化传统的无配体脱羧偶联反应。使用该方法已以中等至良好的产率合成了一系列不对称的二芳基酮。已经提出了涉及酰基自由基的自由基途径。
• Base-free Pd-MOF catalyzed the Suzuki-Miyaura cross-coupling reaction of arenediazonium tetrafluoroborate salts with arylboronic acids
  作者：Yangyang Liu、Jie Wang、Tang Li、Zesheng Zhao、Wan Pang

  DOI：10.1016/j.tet.2019.130540

  日期：2019.10

  (2-pymo)2]n (2-pymo = 2-pyrimidinolate). A series of functionalized biaryl derivatives have been synthesized in good to excellent yields by the Suzuki-miyaura cross-couplings of sustainable arenediazonium salts with a variety of arylboronic acids and the reactions were catalyzed by the Pd-MOF using methanol as a benign solvent. Those base- and additive-free catalytic reactions proceeded smoothly under

  含钯金属-有机骨架（Pd-MOF）[Pd（2-pyMO）2 ] n催化的直接反应证明了联芳基的简便且环境友好的合成（2-pyMO = 2-嘧啶）。Suzuki-miyaura用可持续的芳族重氮鎓盐与各种芳基硼酸的偶联，以良好的产率合成了一系列功能化的联芳基衍生物，并使用甲醇作为良性溶剂，通过Pd-MOF催化了该反应。这些无碱和无添加剂的催化反应在无水和无脱气条件下可顺利进行。这样的转变避免了高反应温度，耐受许多官能团并呈现出宽的底物范围。可以通过过滤回收催化剂，并在MOF结构坍塌之前重复使用四个连续的循环。