potassium thiophen-3-ylethynyltrifluoroborate | 1296155-66-2

• 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 thiophen-3-ylethynyltrifluoroborate
• 英文别名: potassium ((thiophen-3-yl)ethynyl)trifluoroborate
• CAS: 1296155-66-2
• 化学式: C₆H₃BF₃S*K
• 分子量: 214.06
• InChiKey: ZJTLVLUQGBLDSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.51
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  potassium thiophen-3-ylethynyltrifluoroborate 、 3-methoxybenzocyclobutenone 在 bis(1,5-cyclooctadiene)nickel (0) 、 三甲基膦 作用下， 以 甲苯 为溶剂， 以55 %的产率得到5-methoxy-4-(thiophen-3-yl)naphthalen-2-ol
  参考文献：
  名称：

  苯并环丁烯酮与三氟硼酸炔基酯的配体控制镍催化反应：多取代萘酚的多样化构建

  摘要：

  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。

  DOI：

  10.1021/acs.orglett.3c01091
• 作为产物：
  描述：

  3-乙炔基噻吩 、 硼酸三甲酯 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54%的产率得到potassium thiophen-3-ylethynyltrifluoroborate
  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

• Regioselective cycloaddition of potassium alkynyltrifluoroborates with 3-azetidinones and 3-oxetanone by nickel-catalysed C–C bond activation
  作者：Fathi Elwrfalli、Yannick J. Esvan、Craig M. Robertson、Christophe Aïssa

  DOI：10.1039/c8cc09241a

  日期：——

  In the presence of a nickel catalyst, the intermolecular (4+2) cycloaddition of potassium alkynyltrifluoroborates with 3-azetidinones and 3-oxetanone leads to the formation of borylated dihydropyridinones and dihydropyranones without unwanted carbon–boron bond cleavage. The regioselectivity is influenced only by the trifluoroborate group, and only one regioisomer is obtained, whether the other alkyne

  在镍催化剂的存在下，炔基三氟硼酸钾与3-氮杂环丁酮和3-氧杂环丁酮的分子间（4 + 2）环加成反应会导致形成硼化的二氢吡啶并酮和二氢吡喃酮，而不会发生碳-硼键断裂。区域选择性仅受三氟硼酸酯基团影响，并且无论另一个炔烃取代基是烷基，乙烯基或（杂）芳基基团，仅获得一种区域异构体。
• Iridium-catalyzed enantioselective alkynylation and kinetic resolution of alkyl allylic alcohols
  作者：Jia Guo、Hao-Ran Ma、Wen-Bin Xiong、Luoyi Fan、You-Yun Zhou、Henry N. C. Wong、Jian-Fang Cui

  DOI：10.1039/d2sc04892b

  日期：——

  components towards the synthesis of prostaglandins and naturally occurring matsutakeols, which are difficult to access via other asymmetric reactions. Mechanistic studies revealed that the efficient kinetic resolution might be due to the significant distinction of the η2-coordination between the (R)- and (S)-allylic alcohols with the iridium/(phosphoramidite, olefin) complex.

  在此，我们报告了烷基烯丙醇的有效动力学拆分，这是通过烷基烯丙醇与炔基三氟硼酸钾的铱催化对映选择性炔基化实现的。获得了具有各种官能团的各种手性 1,4-烯炔和未反应的富含对映体的烯丙醇，具有出色的对映选择性和高动力学分辨率性能（s因子高达 922）。此外，该方法对于制备一些有用的光学纯烷基烯丙醇特别有效，例如合成前列腺素和天然存在的松茸酚的关键成分，这些成分很难通过其他不对称反应。机理研究表明，有效的动力学拆分可能是由于 ( R )- 和 ( S )- 烯丙醇与铱/（亚磷酰胺，烯烃）络合物之间的η 2配位的显着差异。
• Azido-alkynylation of alkenes through radical-polar crossover
  作者：Julien Borrel、Jerome Waser

  DOI：10.1039/d3sc03309k

  日期：——

  An azido-alkynylation of alkenes has been developed by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. This method allows the synthesis of homopropargylic azides, which could be transformed into pyrroles or bioactive amines.

  通过结合高价碘试剂和炔基三氟硼酸盐，开发出了烯烃的叠氮炔化反应。这种方法可以合成均丙炔基叠氮化物，并可将其转化为吡咯或具有生物活性的胺。
• Organocatalytic Enantioselective Conjugate Alkynylation of β-Aminoenones: Access to Chiral β-Alkynyl-β-Amino Carbonyl Derivatives
  作者：Jian-Fei Wang、Xin Meng、Chao-Huan Zhang、Chuan-Ming Yu、Bin Mao

  DOI：10.1021/acs.orglett.0c02394

  日期：2020.10.2

  Readily available potassium alkynyltrifluoroborates were used for organocatalytic asymmetric conjugate alkynylation of beta-enaminones. The interception of a modified binaphthol catalyst and in situ generated organodifluoroboranes proved important to access functionalized beta-alkynyl-beta-amino carbonyls and derivatives with improved chemo-reactivity and enantio-induction. Mechanistic studies revealed the impact of molecular sieves on efficiency and stereocontrol. The products undergo additional functionalization to yield a diverse set of valuable beta-alkynyl-beta-amino carbonyl scaffolds.
• Iridium-Catalyzed Enantioselective Allylic Alkynylation
  作者：James Y. Hamilton、David Sarlah、Erick M. Carreira

  DOI：10.1002/anie.201302731

  日期：2013.7.15

  No leaving group needed: With an Ir(P,olefin) complex as catalyst, the direct enantioselective allylic alkynylation of secondary allylic alcohols with potassium alkynyltrifluoroborates as alkynylating reagents has been achieved. High levels of enantioselectivity and high yields were achieved with this operationally easy and robust protocol, the use of which was demonstrated in the synthesis of GPR40 receptor agonist AMG 837. cod = 1,5-cyclooctadiene.