2-(phenylselanyl)benzofuran | 1433200-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-(phenylselanyl)benzofuran
• 英文别名: 2-Phenylselanyl-1-benzofuran
• CAS: 1433200-90-8
• 化学式: C₁₄H₁₀OSe
• 分子量: 273.193
• InChiKey: IVXUOXUMAFYQIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-bromo-2-(2-methoxyphenyl)vinylphenylselane 在 copper(I) bromide 作用下， 以 硝基甲烷 为溶剂， 反应 24.0h， 以80%的产率得到2-(phenylselanyl)benzofuran
  参考文献：
  名称：

  乙烯基硒化物的分子内环化反应合成2-（芳基硒基）苯并[b]硫属元素芴

  摘要：

  摘要 描述了一种通过Cu（I）催化的乙烯基硒化物的环化反应获得2-芳基硒基苯并[ b ]硫属元素衍生物的有效方案。关键的乙烯基硒化物可以容易地由适当官能化的1,1-二溴苯乙烯制备，并且该方法允许以中等至优异的产率合成2-芳基硒基呋喃，-噻吩和-硒代苯。 描述了一种通过Cu（I）催化的乙烯基硒化物的环化反应获得2-芳基硒基苯并[ b ]硫属元素衍生物的有效方案。关键的乙烯基硒化物可以容易地由适当官能化的1,1-二溴苯乙烯制备，并且该方法允许以中等至优异的产率合成2-芳基硒基呋喃，-噻吩和-硒代苯。

  DOI：

  10.1055/s-0037-1610656

文献信息

• Synthesis of 2-selenyl(sulfenyl)benzofurans via Cu-catalyzed tandem reactions of 2-(gem-dibromovinyl)phenols with diorganyl diselenides(disulfides)
  作者：Jie Liu、Wei Chen、Lei Wang

  DOI：10.1039/c3ra23361h

  日期：——

  An efficient synthesis of 2-selenyl(sulfenyl)benzofurans has been accomplished through a copper(I)-catalyzed tandem reaction of 2-(gem-dibromovinyl)phenols with diorganyl diselenides and disulfides in the presence of CuI/Mg/t-BuOLi in DMSO. Using this protocol, a variety of 2-selenyl(sulfenyl)benzofuran derivatives were obtained in good yields.

  已通过铜(I)催化的串联反应，高效合成了2-硒基（硫醇基）苯并呋喃，该反应是将2-（gem-二溴乙烯基）苯酚与二有机基二硒化物和二硫化物在CuI/Mg/t-BuOLi的存在下于DMSO中进行的。采用该方法，获得了多种2-硒基（硫醇基）苯并呋喃衍生物，产率良好。
• UVA Light‐promoted Catalyst‐free Cyclization of Vinyl Selenides: Green and Efficient Synthesis of C3‐Unsubstituted 2‐Selanyl Benzochalcogenophenes
  作者：Gelson Perin、Thiago J. Peglow、Filipe Penteado、Patrick C. Nobre、Krigor B. Silva、Guilherme Stach、Thiago Barcellos、Eder J. Lenardão、Juliano A. Roehrs

  DOI：10.1002/asia.202101394

  日期：2022.4.14

  An environmentally friendly protocol to prepare selenium-containing benzo[b]chalcogenophenes by photocyclization of o-chalcogen-substituted selanylalkenes using UVA irradiation is presented.

  提出了一种利用 UVA 辐照光环化邻硫属取代的硒基烯烃制备含硒苯并[ b ]硫属烯的环保方案。
• Electrochemical Generation of Aryl Radicals from Organoboron Reagents Enabled by Pulsed Electrosynthesis
  作者：Maxime Boudjelel、Jessica Zhong、Lorenzo Ballerini、Ian Vanswearingen、Rossul Al‐Dhufari、Christian A. Malapit

  DOI：10.1002/anie.202406203

  日期：2024.7.29

  Pulsed electrosynthesis efficiently converts aromatic organoboron reagents to aryl radicals. Mechanistic studies reveal that pulsed electrosynthesis overcomes challenges like radical grafting/passivation, homocoupling, overoxidation, and decomposition. This electro-oxidative method enables straightforward functionalization of aromatic organoboron reagents to form aryl C−P, C−Se, C−Te, and C−S bonds

  脉冲电合成有效地将芳香族有机硼试剂转化为芳基自由基。机理研究表明，脉冲电合成克服了自由基接枝/钝化、自偶联、过度氧化和分解等挑战。这种电氧化方法能够直接官能化芳香族有机硼试剂，形成芳基 C−P、C−Se、C−Te 和 C−S 键。
• A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature
  作者：Amit Kumar、Sangit Kumar

  DOI：10.1016/j.tet.2014.01.030

  日期：2014.3

  A simple and convenient approach for the synthesis of unsymmetrical diaryl chalcogenides (Te, Se, and S) has been developed by copper-catalyzed cross-coupling reaction of organoboronic acid with diaryl dichalcogenide in ethanol using NaBH4 in air or oxygen. The present methodology is highly practical for the synthesis of unsymmetrical diaryl tellurides with various functionalities such as -NO2, -F, -Br, and -COOH that have been obtained in good to excellent yields. Methodology is also effective for the synthesis of unsymmetrical diaryl selenides and sulfides. Moreover, symmetrical diaryl selenides have also been obtained from arylboronic acids using elemental selenium powder under optimized reaction conditions. The use of NaBH4 is the key for the development of milder reaction conditions, which enable the construction of unsymmetrical diaryl chalcogenides from boronic acid substrates in ethanol at room temperature. (C) 2014 Elsevier Ltd. All rights reserved.
• Copper-catalyzed C–Se coupling of diphenyl diselenide with arylboronic acids at room temperature
  作者：Bo Zheng、Ying Gong、Hua-Jian Xu

  DOI：10.1016/j.tet.2013.04.124

  日期：2013.7

  An efficient synthetic protocol for the Cu-catalyzed cross-coupling of diphenyl diselenide and arylboronic acid at room temperature was described. This catalytic system could tolerate a variety of arylboronic acids with only 3 mol % amount of CuSO4 as the catalyst and inexpensive 1,10-phen. H2O as the ligand. Moreover, this catalytic system used environment-friendly EtOH as the solvent and catalytic amount of Na2CO3 (20 mol %) as the base in the air. (C) 2013 Elsevier Ltd. All rights reserved.