2-(4-acetylphenyl)-1,3,2-dioxaborinane | 156942-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-acetylphenyl)-1,3,2-dioxaborinane
• 英文别名: 1-[4-(1,3,2-dioxaborinan-2-yl)phenyl]ethanone
• CAS: 156942-22-2
• 化学式: C₁₁H₁₃BO₃
• 分子量: 204.033
• InChiKey: CPNXAMQOWQHBPS-UHFFFAOYSA-N

物化性质

• 沸点：
  362.5±25.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-acetylphenyl)-1,3,2-dioxaborinane 、 3-氨基异噁唑-5-羧酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 silver carbonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 4.0h， 以36%的产率得到1-(4-(piperidine-1-carbonyl)phenyl)ethanone
  参考文献：
  名称：

  硫脲和芳基硼酸的钯催化脱硫酰胺形成

  摘要：

  卡宾配合物的反应性的发展将导致创建新的合成策略。我们在本文中发现Pd催化的脱硫酰胺形成涉及Suzuki-Miyaura偶联反应，特别是Pd配合物是由硫脲，Ag盐和Pd催化剂原位生成的。银盐对于从可用的和稳定的硫脲构建此类卡宾是必不可少的，并且很好地参与了催化循环。我们报道了一种由芳基硼酸合成芳基酰胺的方法，该方法极大地丰富了硫脲化学的应用并扩展了Suzuki-Miyaura偶联的应用。

  DOI：

  10.1002/cctc.202001099
• 作为产物：
  描述：

  4-溴苯乙酮 、 1,3-丙二醇 在 四(三苯基膦)钯 、 四次甲氨基乙硼烷 、 potassium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 22.0h， 生成 2-(4-acetylphenyl)-1,3,2-dioxaborinane
  参考文献：
  名称：

  [EN] PROCESS FOR THE BORYLATION OF ORGANOHALIDES
  [FR] PROCÉDÉ POUR LA BORYLATION D'ORGANOHALOGÉNURES

  摘要：

  本发明涉及一种有机卤化物硼化的方法。

  公开号：

  WO2013014579A1

文献信息

• Borylation of organo halides and triflates using tetrakis(dimethylamino)diboron
  作者：Charles S. Bello、Joachim Schmidt-Leithoff

  DOI：10.1016/j.tetlet.2012.09.009

  日期：2012.11

  We report a new in situ borylation method using tetrakis(dimethylamino)diboron, DMA4B2, in the presence of a diol. Our method uses standard borylation conditions and readily available Pd-catalysts. The scope of this method includes aryl halides and triflates as well as vinyl halides and triflates. The method successfully works with a broad range of diols, enabling the selection of the best boronic

  我们报告了一种新的原位硼化方法，使用四（二甲基氨基）二硼，DMA 4 B 2，在二醇的存在下。我们的方法使用标准的硼化条件和现成的Pd催化剂。该方法的范围包括芳基卤化物和三氟甲磺酸酯以及乙烯基卤化物和三氟甲磺酸酯。该方法成功地与多种二醇一起使用，从而能够为随后的Suzuki偶联选择最佳的硼酸酯。
• A new facile synthesis of 2-substituted 1,3-butadiene derivatives via palladium-catalyzed cross-coupling reaction of 2,3-alkadienyl carbonates with organoboron compounds
  作者：Tsukasa Moriya、Toshinari Furuuchi、Norio Miyaura、Akira Suzuki

  DOI：10.1016/s0040-4020(01)85281-9

  日期：1994.1

  A synthesis of 2-aryl-, 2-(1-alkenyl)-, and 2-alkyl-1,3-butadiene derivatives (2) by the palladium-catalyzed cross-coupling reaction of 2,3-butadienyl carbonates (1) with 9-alkyl-9-bicyclo[3.3.1]nonanes (9-alkyl-9-BBN), 1-alkenylboronic acids, or arylboronic acids is described. The reaction proceeded regioselectively with the palladium-phosphine complexes under neutral conditions.

  和2-烷基-1,3-丁二烯衍生物（ - 2-芳基- ，2-（1-烯基）的合成2由2,3-丁二烯基碳酸酯的钯催化交叉偶联反应）（1）描述了具有9-烷基-9-双环[3.3.1]壬烷（9-烷基-9-BBN），1-烯基硼酸或芳基硼酸的烷氧基。该反应与钯-膦配合物在中性条件下区域选择性地进行。
• Nickel-Catalyzed Addition of Organoboronates to 1,2-Dienes and the Corresponding Three-Component Reaction with an Alkyne
  作者：Go Takahashi、Eiji Shirakawa、Teruhisa Tsuchimoto、Yusuke Kawakami

  DOI：10.1002/adsc.200505445

  日期：2006.5

  A Ni(cod)2–aminophosphine complex catalyzed the addition of aryl- and alkenylboronates to 1,2-dienes to give the hydroarylation and hydroalkenylation products of the 1,2-dienes, whereas the hydroarylation products of a 1,2-diene and an alkyne were obtained with a Ni(cod)2–PPh3 catalyst.

  Ni（cod）2-氨基膦配合物催化将芳基和链烯基硼酸酯加成至1,2-二烯，得到1,2-二烯的加氢芳基化和加氢烯基化产物，而1,2-二烯和使用Ni（cod）2 -PPh 3催化剂获得炔烃。
• Alkynes as activators in the nickel-catalysed addition of organoboronates to aldehydes
  作者：Go Takahashi、Eiji Shirakawa、Teruhisa Tsuchimoto、Yusuke Kawakami

  DOI：10.1039/b417353h

  日期：——

  Alkynes act not as substrates but as co-catalysts in the presence of a nickel catalyst, an organoboronate and an aldehyde to promote the addition reaction between the substrates in combination with H2O.

  炔烃不是底物，而是在镍催化剂、有机硼酸盐和醛的存在下作为助催化剂，促进底物与 H2O 的加成反应。
• Mechanistic Investigations and Substrate Scope Evaluation of Ruthenium-Catalyzed Direct sp³ Arylation of Benzylic Positions Directed by 3-Substituted Pyridines
  作者：Navid Dastbaravardeh、Karl Kirchner、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1021/jo302547q

  日期：2013.1.18

  A highly efficient direct arylation process of benzylic amines with arylboronates was developed that employs Ru catalysis. The arylation takes place with greatest efficiency at the benzylic sp(3) carbon. If the distance to the activating aryl ring is increased, arylation is still possible but the yield drops significantly. Efficiency of the CH activation was found to be significantly increased by use of 3-substituted pyridines as directing groups, which can be removed after the transformation in high yield. Calculation of the energy profile of different rotamers of the substrate revealed that presence of a substituent in the 3-position favors a conformation with the CH2 group adopting a position in closer proximity to the directing group and facilitating C-H insertion. This operationally simple reaction can be carried out in argon atmosphere as well as in air and under neutral reaction conditions, displaying a remarkable functional group tolerance. Mechanistic studies were carried out and critically compared to mechanistic reports of related transformations.