(4-tert-butylphenyl)diazonium tetrafluoroborate | 52436-75-6

• 英文名称: (4-tert-butylphenyl)diazonium tetrafluoroborate
• 英文别名: p-tert-butylphenyldiazonium tetrafluoroborate salt；4-(tert-butyl)benzenediazonium tetrafluoroborate；4-tert-butylbenzenediazonium tetrafluoroborate；p-tert-butylbenzenediazonium tetrafluoroborate；4-tert-butylphenyldiazonium tetrafluoroborate；4-tertbutylbenzenediazonium tetrafluoroborate
• CAS: 52436-75-6
• 化学式: BF₄*C₁₀H₁₃N₂
• 分子量: 248.031
• InChiKey: RQJQVHGXUDXFJI-UHFFFAOYSA-N

计算性质

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

• 作为反应物：
  描述：

  (4-tert-butylphenyl)diazonium tetrafluoroborate 在 叠氮基三甲基硅烷 、 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 以98%的产率得到1-azido-4-tert-butylbenzene
  参考文献：
  名称：

  Halo- and Azidodediazoniation of Arenediazonium Tetrafluoroborates with Trimethylsilyl Halides and Trimethylsilyl Azide and Sandmeyer-Type Bromodediazoniation with Cu(I)Br in [BMIM][PF₆] Ionic Liquid

  摘要：

  [GRAPHICS]Reaction of [ArN2][BF4] salts immobilized in [BMIM][PF6] ionic liquid (IL) with TMSX (X = 1, Br) and TMSN3 represents an efficient method for the preparation of iodo-, bromo-, and azido-derivatives via dediazoniation. The reactions can also be effected starting with ArNH2 by in situ diazotization with [NO][BF4] followed by reaction with TMSX or TMSN3. Depending on the substituents on the benzenediazonium cation, competing fluorodediazoniation (ArF formation) and hydrodediazoniation (ArH formation) were observed. Dediazoniation with TMSN3 and with TMSI generally gave the highest chemoselectivity toward ArN3 and ArI formation. The IL was recycled and reused up to 5 times with no appreciable decrease in the conversions. Multinuclear NMR monitoring of the interaction of [ArN2][BF4]/TMSX, [BMIM][PF6]/TMSX, and [BMIM][PF6]/TMSX/[ArN2][BF4] indicated that TMSF is formed primarily via [ArN2][BF4]/TMSX, generating [ArN2][X] in situ, which gives ArX on dediazoniation. Competing formation of ArF in Sandmeyer-type bromodediazoniation of [ArN2][BF4] with Cu(I)Br immobilized in the IL points to significant involvement of heterolytic dediazoniation.

  DOI：

  10.1021/jo701937e
• 作为产物：
  描述：

  4-叔丁基苯胺 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 生成 (4-tert-butylphenyl)diazonium tetrafluoroborate
  参考文献：
  名称：

  芳基重氮阳离子的手性阴离子相转移：C3-重氮吡咯并二氢吲哚的对映选择性合成

  摘要：

  本文首次报道了芳基重氮阳离子作为亲电子氮源的不对称利用。这是通过手性阴离子相转移吡咯并吲哚化反应实现的，该反应从简单的色胺和芳基重氮四氟硼酸盐形成 C3-重氮化吡咯并吲哚。标题化合物的产率高达 99%，ee高达 96%  。耐空气和耐水反应允许芳基重氮亲电试剂和色胺核的电子和空间多样性。

  DOI：

  10.1002/anie.201310905

文献信息

• Hypervalent Iodine(III)-Catalyzed Balz-Schiemann Fluorination under Mild Conditions
  作者：Bo Xing、Chuanfa Ni、Jinbo Hu

  DOI：10.1002/anie.201802466

  日期：2018.7.26

  An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional‐group compatibility.

  描述了前所未有的高价碘（III）催化的Balz-Schiemann反应。在存在高价碘化合物的情况下，氟化反应会在温和的条件下（25–60°C）进行，并且具有广泛的底物范围和良好的官能团相容性。
• Fluorosulfonylation of arenediazonium tetrafluoroborates with Na2S2O5 and N-fluorobenzenesulfonimide
  作者：Shuai Liu、Yangen Huang、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1016/j.jfluchem.2020.109653

  日期：2020.12

  the three-component reaction of arenediazonium tetrafluoroborates, Na2S2O5, and N-fluorobenzenesulfonimide (NFSI). The reaction proceeds through a radical tandem process, affording various arenesulfonyl fluorides in moderate to high yields. This protocol not only provides a complement to the previous fluorosulfonylation reactions, but also extends the applications of Sandmeyer reaction.

  通过四氟硼酸壬二唑鎓，Na 2 S 2 O 5和N-氟苯磺酰亚胺（NFSI）的三组分反应，实现了无过渡金属的Sandmeyer型氟磺酰化反应。该反应通过自由基串联过程进行，以中等至高产率提供各种芳烃磺酰氟。该方案不仅为以前的氟磺酰化反应提供了补充，而且扩展了桑德迈尔反应的应用。
• Preparation of Ketimines from Aryldiazonium Salts, Arenes, and Nitriles via Intermolecular Arylation of <i>N</i>-Arylnitrilium Ions
  作者：Mani Ramanathan、Yu-Hao Wang、Yi-Hung Liu、Shie-Ming Peng、Yuan-Chung Cheng、Shiuh-Tzung Liu

  DOI：10.1021/acs.joc.8b01000

  日期：2018.6.1

  three-component strategy offers a step- and atom-efficient way to N-arylketimines from easily accessible reagents under mild reaction conditions. The characterization of stereochemistry of ketimine was achieved by X-ray crystallographic structure and theoretical calculation. Operational simplicity, shorter reaction time, excellent functional group compatibility, and scalability are the key features of this

  芳族重氮盐，芳烃和腈的直接反应以一锅法与N-C和C-C键连续形成的方式开发了一种无过渡金属的N-芳基酮亚胺制备方法。该方法通过原位产生N-芳基腈中间产物进行，然后进行分子间芳基化。这种三成分策略为实现N提供了一种分步高效且原子效率高的方法-芳基酮亚胺，在温和的反应条件下容易获得的试剂。通过X射线晶体结构和理论计算对酮亚胺的立体化学进行表征。操作简便，反应时间短，出色的功能组兼容性和可扩展性是本报告的主要功能。
• Iridium-Catalyzed<i>ortho</i>-Arylation of Benzoic Acids with Arenediazonium Salts
  作者：Liangbin Huang、Dagmar Hackenberger、Lukas J. Gooßen

  DOI：10.1002/anie.201505769

  日期：2015.10.19

  In the presence of catalytic [IrCp*Cl2}2] and Ag2CO3, Li2CO3 as the base, and acetone as the solvent, benzoic acids react with arenediazonium salts to give the corresponding diaryl‐2‐carboxylates under mild conditions. This CH arylation process is generally applicable to diversely substituted substrates, ranging from extremely electron‐rich to electron‐poor derivatives. The carboxylate directing

  在催化[IrCp * Cl 2 } 2 ]和Ag 2 CO 3，Li 2 CO 3为碱，丙酮为溶剂的情况下，苯甲酸与槟榔重氮盐反应生成相应的二芳基-2-羧酸盐温和的条件。这种CH芳基化过程通常适用于各种取代的底物，范围从极富电子的至贫电子的衍生物。羧酸根导向基团是广泛可得的，可以无痕地除去或用于进一步的衍生作用。通过使用重氮盐可实现与卤化物交叉偶联的正交性，即使存在碘取代基也可将其偶联。
• Palladium-catalyzed direct sulfonylation of C–H bonds with the insertion of sulfur dioxide
  作者：Hongguang Xia、Yuanyuan An、Xincheng Zeng、Jie Wu

  DOI：10.1039/c7cc07279a

  日期：——

  A palladium-catalyzed direct sulfonylation of C–H bonds with the insertion of sulfur dioxide under mild conditions is reported. The sulfonylative couplings with the insertion of sulfur dioxide into C–H bonds are effective, and two classes of sulfonylative products are formed in moderate to good yields by the combination of radical chemistry and palladium-catalyzed C–H activation.

  据报道，在温和的条件下，钯催化了C–H键的直接磺酰化反应，并插入了二氧化硫。通过将二氧化硫插入C–H键中的磺酰化偶联是有效的，并且通过自由基化学和钯催化的C–H活化的结合，以中等至良好的产率形成了两类磺化产物。