potassium styryltrifluoroborate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: potassium styryltrifluoroborate
• 英文别名: Potassium styryltrifluoroborate；potassium;trifluoro(2-phenylethenyl)boranuide
• 化学式: C₈H₇BF₃*K
• 分子量: 210.048
• InChiKey: NONAUTDEFRJJII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium styryltrifluoroborate 在 sodium dihydrogenphosphate dihydrate 、 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 、 sodium nitrite 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以92%的产率得到β-硝基苯乙烯
  参考文献：
  名称：

  A novel route to organonitrites by Pd-catalyzed cross-coupling of sodium nitrite and potassium organotrifluoroborates

  摘要：

  Microwave irradiated palladium-catalyzed cross-coupling reaction of potassium styryltrifluoroborates and sodium nitrite gives the corresponding styryl nitrites in high yields. Potassium aryltrifluoroborates also furnish aryl nitrites under same reaction condition. This unprecedented cross-coupling is an interesting development and has the potential to lead to new nitration protocols. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.047
• 作为产物：
  描述：

  苯乙炔 在 Wilkinson's catalyst 儿萘酚硼烷 、 potassium hydrogen bifluoride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙醚 、 水 为溶剂， 反应 2.33h， 以19%的产率得到potassium styryltrifluoroborate
  参考文献：
  名称：

  Suzuki Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates

  摘要：

  GRAPHICSThe palladium-catalyzed coupling reaction of potassium alkenyltrifluoroborates with aryl or alkenyl halides or triflates proceeds readily with good yields. The trifluoroborates are air- and moisture-stable solids that can be stored indefinitely. The cross-coupling can be effected using PdCl2(dppf).CH2Cl2 as the catalyst in n-PrOH in the presence of Et3N. A variety of functional groups are tolerated.

  DOI：

  10.1021/ol0169729

文献信息

• Sunlight-driven trifluoromethylation of olefinic substrates by photoredox catalysis: A green organic process
  作者：Munetaka Akita、Takashi Koike

  DOI：10.1016/j.crci.2015.01.013

  日期：2015.7

  types of catalytic photoredox processes following the reductive quenching cycle (RQC) and the oxidative quenching cycle (OQC), the discussion is focused on organic transformations based on OQC, in particular the trifluoromethylation of olefinic substrates with electrophilic trifluoromethylating reagents furnishing solvolytic addition products and substitution products. It is concluded that catalytic

  摘要 描述了光氧化还原催化在有机合成中的原理和应用。在简要描述了还原淬灭循环 (RQC) 和氧化淬灭循环 (OQC) 之后的两种催化光氧化还原过程的特征后，讨论的重点是基于 OQC 的有机转化，特别是烯烃底物的三氟甲基化与亲电三氟甲基化试剂一起提供溶剂分解加成产物和取代产物。得出的结论是，从危害性、安全性和能源（可见光，包括阳光）的角度来看，催化光氧化还原系统是绿色的。还将讨论光氧化还原催化的未来前景。
• Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations
  作者：Qilei Zhu、Emily C. Gentry、Robert R. Knowles

  DOI：10.1002/anie.201604619

  日期：2016.8.16

  weak C−O bond. Spontaneous scission results in the formation of the stable nitroxyl radical TEMPO. as well as a reactive carbocation intermediate that can be intercepted by a wide range of nucleophiles. Notably, this process occurs under neutral conditions and at comparatively mild potentials, enabling catalytic cation generation in the presence of both acid sensitive and easily oxidized nucleophilic

  描述了一种新的催化方法，该方法通过烷氧基胺自由基阳离子的介观裂解来获得碳正离子中间体。在此过程中，激发态氧化剂与TEMPO衍生的烷氧基胺底物之间的电子转移会产生带有非常弱的C-O键的自由基阳离子。自发断裂导致形成稳定的硝基自由基TEMPO 。以及可被多种亲核试剂截获的反应性碳正离子中间体。值得注意的是，该过程在中性条件下和相对温和的电势下发生，从而在酸敏感和易氧化的亲核分子同时存在的情况下能够产生催化阳离子。
• A Deacetylation-Diazotation-Coupling Sequence: Palladium- Catalyzed CC Bond Formation with Acetanilides as Formal Leaving Groups
  作者：Bernd Schmidt、René Berger

  DOI：10.1002/adsc.201200929

  日期：2013.2.1

  Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki cross-coupling reactions, and a Pd-catalyzed [2+2+1] cycloaddition have been investigated as terminating CC bond-forming steps of this one-flask sequence. The sequence does not require the exchange of solvents or removal

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• Directed <i>ortho</i>-metalation–nucleophilic acyl substitution strategies in deep eutectic solvents: the organolithium base dictates the chemoselectivity
  作者：Simone Ghinato、Giuseppe Dilauro、Filippo Maria Perna、Vito Capriati、Marco Blangetti、Cristina Prandi

  DOI：10.1039/c9cc03927a

  日期：——

  Directed ortho metalation (DoM) or nucleophilic acyl substitution (SNAc) can be efficiently programmed on the same aromatic carboxylic acid amide, in a choline chloride-based eutectic mixture, by simply switching the nature of the organolithium reagent. Telescoped, one-pot ortho-lithiation/Suzuki–Miyaura cross-couplings have also been demonstrated for the first time in Deep Eutectic Solvents.

  定向邻位金属化（d Ò M）或亲核酰基取代（S Ñ AC）可以有效地设定为在同芳族羧酸酰胺，在基于氯化物胆碱共熔混合物，通过简单地切换有机锂试剂的性质。伸缩式单罐正锂化/铃木-宫浦交叉联结也已在深共晶溶剂中首次得到证明。
• Synthesis of Unsymmetrical Diorganyl Chalcogenides under Greener Conditions: Use of an Iodine/DMSO System, Solvent- and Metal-Free Approach
  作者：Sumbal Saba、Jamal Rafique、Antonio L. Braga

  DOI：10.1002/adsc.201500024

  日期：2015.5.4

  Herein, we report a greener iodine‐catalyzed protocol to access different types of unsymmetrical diorganyl chalcogenides. This new approach works in the absence of solvent and metal. The desired products were obtained in good to excellent yields using one equivalent of arylboronic acids, half an equivalent of various diorganyl dichalcogenides, iodine (10 mol%) as a catalyst and 2 equivalents of dimethyl

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