potassium [(4-ethylphenyl)ethynyl]trifluoroborate

• 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 [(4-ethylphenyl)ethynyl]trifluoroborate
• 英文别名: potassium (4-ethylphenyl)ethynyltrifluoroborate；Potassium;2-(4-ethylphenyl)ethynyl-trifluoroboranuide
• 化学式: C₁₀H₉BF₃*K
• 分子量: 236.086
• InChiKey: BUGJBEIGMZJJCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.01
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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 [(4-ethylphenyl)ethynyl]trifluoroborate 、 Langlois reagent 在 叔丁基过氧化氢 、 碳酸氢钠 、 copper(l) chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 以56%的产率得到1-ethyl-4-(3,3,3-trifluoroprop-1-ynyl)benzene
  参考文献：
  名称：

  Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent

  摘要：

  Synthesis of trifluoromethylated acetylenes by copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with CF3 radicals generated from NaSO2CF3 and tert-butyl hydroperoxide (TBHP) is communicated. The trifluoromethylated acetylenes were obtained in good to moderate yields. The presented method tolerates a wide range of aromatic, heteroaromatic, and aliphatic potassium alkynyltrifluoroborates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.005
• 作为产物：
  描述：

  硼酸三甲酯 、 4-乙基苯乙炔 在 正丁基锂 、 二氟化氢钾 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 5.0h， 以58%的产率得到potassium [(4-ethylphenyl)ethynyl]trifluoroborate
  参考文献：
  名称：

  Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent

  摘要：

  Synthesis of trifluoromethylated acetylenes by copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with CF3 radicals generated from NaSO2CF3 and tert-butyl hydroperoxide (TBHP) is communicated. The trifluoromethylated acetylenes were obtained in good to moderate yields. The presented method tolerates a wide range of aromatic, heteroaromatic, and aliphatic potassium alkynyltrifluoroborates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.005

文献信息

• Lewis acid promoted Mannich type reactions of α,α-dichloro aldimines with potassium organotrifluoroborates
  作者：Sara Stas、Kourosch Abbaspour Tehrani

  DOI：10.1016/j.tet.2007.06.003

  日期：2007.9

  Potassium phenylethynyltrifluoroborate and potassium styryltrifluoroborates react with α,α-dichlorinated aldimines in the presence of BF3·OEt2 as a Lewis acid to give a new stable class of functionalized propargylamines and allylamines. The use of hexafluoroisopropanol as a co-solvent in this modified Petasis reaction allows high yield isolation of the target compounds.

  苯基乙炔基三氟硼酸钾和苯乙烯基三氟硼酸钾在BF 3 ·OEt 2作为路易斯酸的存在下与α，α-二氯醛亚胺反应，得到一类新的稳定的官能化炔丙基胺和烯丙胺。在该改进的Petasis反应中使用六氟异丙醇作为助溶剂可实现目标化合物的高收率分离。
• Fluoroaziridines as novel substrates in the modified Petasis reaction: synthesis of monofluorinated propargyl amines
  作者：Alexander S. Konev、Sara Stas、Mikhail S. Novikov、Alexander F. Khlebnikov、Kourosch Abbaspour Tehrani

  DOI：10.1016/j.tet.2007.10.067

  日期：2008.1

  Reaction of 2-fluoroaziridines with potassium alkynyltrifluoroborates in the presence of BF3·OEt2 leads to fluorinated propargyl amines in moderate to good yields. The reaction proceeds as an in situ isomerization of 2-fluoroaziridines to α-fluorinated imines, followed by the reaction of the imine with alkynyldifluoroborane, which is generated in situ from the potassium alkynyltrifluoroborates and

  在BF 3 ·OEt 2的存在下，2-氟氮丙啶与炔基三氟硼酸钾的反应以中等至良好的产率生成氟化的炔丙基胺。该反应以2-氟氮丙啶的原位异构化为α-氟化亚胺的方式进行，然后亚胺与炔基二氟硼烷的反应，该炔基二氟硼烷是由炔基三氟硼酸钾和BF 3 ·OEt 2原位生成的。
• Ligand-Controlled Nickel-Catalyzed Reactions of Benzocyclobutenones with Alkynyltrifluoroborates: Diverse Construction of Polysubstituted Naphthols
  作者：Yuhang Wang、Peng Ma、Ning Ma、Jianhui Wang

  DOI：10.1021/acs.orglett.3c01091

  日期：2023.5.19

  the ligand led to predictably divergent synthesis of a wide range of 1-naphthols and 2-naphthols without C2 and C3 substituents, respectively, from BCBs and potassium alkynyltrifluoroborate, and the increase in the amount of PMe3 resulted in tandem reaction of 2 equiv of BCB with the borate to afford 3,4,5-trisubstituted 2-naphthols. The fabulous ligand effect resulted in the facile and unique construction

  据报道，配体控制的镍催化选择性裂解苯并环丁烯酮 (BCB) 的 C1–C2 或 C1–C8 键。精心选择 dpppe 或 PMe 3作为配体，可预测地分别从 BCB 和炔基三氟硼酸钾合成各种不含 C2 和 C3 取代基的 1-萘酚和 2-萘酚，并增加 PMe 的量3导致 2 当量 BCB 与硼酸盐的串联反应，得到 3,4,5-三取代的 2-萘酚。令人难以置信的配体效应导致多取代萘酚的简单和独特的构建，具有良好控制的区域选择性和高度的结构多样性。
• Carbon–carbon bond formation via a tandem cationic 2-aza-Cope rearrangement–Lewis acid promoted Petasis reaction
  作者：Sara Stas、Kourosch Abbaspour Tehrani、Georges Laus

  DOI：10.1016/j.tet.2008.02.025

  日期：2008.4

  Potassium alkynyltrifluoroborates and potassium (2-phenyl)vinyltrifluoroborates react with N-3-butenyl-(2,2-dichloro-1-propylidene)amine in the presence of BF3 center dot Et2O as a Lewis acid to synthesize rearranged Mannich products. The reaction starts with a cationic 2-aza-Cope rearrangement of the imine, followed by the Lewis acid promoted borono-Mannich-type reaction on the rearranged imine to result in a new class of functionalized N-homoallylamines. (c) 2008 Elsevier Ltd. All rights reserved.
• Monofluorinated aziridines in asymmetric synthesis of chiral fluorinated prop-2-yn-1-amines
  作者：A. S. Konev、K. Abbaspour Tehrani、A. F. Khlebnikov、M. S. Novikov、J. Magull

  DOI：10.1134/s1070428010070043

  日期：2010.7

  Nonracemic C-fluoroaziridines were synthesized for the first time by reaction of fluorocarbene with N-diphenylmethylidene-substituted natural amino acid esters. The products were shown to be used in asymmetric synthesis of chiral fluorinated prop-2-yn-1-amines via one-pot process involving isomerization of 2-fluoroaziridines into alpha-fluoro imines and subsequent reaction with alkynyldifluoroborane generated in situ.