methylphenylphosphine-borane

• 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: methylphenylphosphine-borane
• 英文别名: borane;methyl(phenyl)phosphane
• 化学式: BH₃*C₇H₉P
• 分子量: 137.957
• InChiKey: NGYSEIKGPPLANO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1-辛炔 、 methylphenylphosphine-borane 在 palladium diacetate 1,3-双(二苯基膦)丙烷 作用下， 以 甲苯 为溶剂， 反应 35.0h， 以85%的产率得到2-(boranatomethylphenylphosphino)oct-1-ene
  参考文献：
  名称：

  炔与膦-硼烷的区域和立体选择性加氢磷酸化反应：获得立体定义的乙烯基膦衍生物。

  摘要：

  乙烯基膦-硼烷配合物可通过使用仲膦-硼烷作为氢膦化剂，通过末端炔的区域和立体选择性加氢磷酸化而容易地合成。通过选择活化过程可以有效控制反应的区域选择性：热或金属催化剂活化。通过硅胶色谱法纯化乙烯基膦衍生物。该过程的可扩展性以克为单位进行了证明。这种简单的方法应该促进使用乙烯基膦作为有机和有机金属化学的基础。

  DOI：

  10.1021/jo030096q
• 作为产物：
  描述：

  甲基溴化镁 、 phenylmagnesium bromide 生成 methylphenylphosphine-borane
  参考文献：
  名称：

  High Atom-Economical One-Pot Synthesis of Secondary Phosphines and Their Borane Complexes Using Recycling Phosphorus Donor Reagent

  摘要：

  A general new method for the one-pot preparation of secondary phosphines 11 and in situ generation of their borane complexes 12 is described. This method consists of the sequential addition, at room temperature, of equivalent amounts of (RMgBr)-Mg-1 and (RMgBr)-Mg-2 to 1 equiv of the phosphorus atom donor reagent 1. Final treatment with water gives secondary phosphines (RRPH)-R-1-P-2 (or the corresponding phosphine-borane complexes if treated with BH3-THF) and the end product 6, which can be recycled.

  DOI：

  10.1021/ol060284d

文献信息

• Palladium-Catalyzed C−P Coupling Reactions between Vinyl Triflates and Phosphine−Boranes:  Efficient Access to Vinylphosphine−Boranes
  作者：Delphine Julienne、Jean-François Lohier、Olivier Delacroix、Annie-Claude Gaumont

  DOI：10.1021/jo062482o

  日期：2007.3.1

  complexes are easily synthesized by palladium-catalyzed C−P cross-coupling of vinyl triflates with secondary phosphine−boranes. This method allows the synthesis of phosphine derivatives not always easily accessible by other approaches. The vinylphosphine derivatives are purified by chromatography on silica gel. The versatility of the method is proved by using various triflates and diaryl-, dialkyl- and al

  乙烯基膦-硼烷络合物很容易通过钯催化的乙烯基三氟甲磺酸酯与仲膦-硼烷的CP交叉偶联而合成。该方法使得膦衍生物的合成并非总是可以通过其他方法容易地获得。通过硅胶色谱法纯化乙烯基膦衍生物。通过使用各种三氟甲磺酸酯和二芳基-，二烷基-和烷基芳基膦-硼烷前体证明了该方法的多功能性。手性对映体纯的膦硼烷是从手性三氟甲磺酸酯合成的。
• Regioselective uncatalysed hydrophosphination of alkenes: a facile route to P-alkylated phosphine derivatives
  作者：David Mimeau、Olivier Delacroix、Annie-Claude Gaumont

  DOI：10.1039/b311892d

  日期：——

  The synthesis of alkylarylphosphines is easily carried out by hydrophosphination of unactivated alkenes under mild thermal activation; gram scale amounts of products can be prepared by this simple methodology.

  烷基芳基膦的合成很容易在温和的热活化条件下将未活化的烯烃加氢磷酸化。克量的产品可以通过这种简单的方法制备。
• Mild and Simple Preparation of Ketophosphine-boranes through Uncatalysed Hydrophosphination of Enones
  作者：Annie-Claude Gaumont、Benoît Join、Olivier Delacroix

  DOI：10.1055/s-2005-871576

  日期：——

  simple method for the synthesis of γ-ketophosphines is reported. This method is based on the atom efficient hydrophosphination reaction using secondary phosphine-boranes as precursors. Different examples with various substrates and phosphine precursors are described. The reaction occurs without any catalyst upon simple thermal activation (50-80 °C). Reduction of a γ-ketophosphine yields in good yield and

  报道了一种有效且简单的合成γ-酮膦的方法。该方法基于使用仲膦-硼烷作为前体的原子高效氢膦化反应。描述了具有各种底物和膦前体的不同例子。在简单的热活化 (50-80 °C) 下，该反应无需任何催化剂。γ-酮膦产量的减少以良好的收率和优异的非对映选择性得到一种新的羟基膦。
• IMAMOTO, TSUNEO;OSHIKI, TOSHIYUKI;ONOZAWA, TAKASHI;KUSUMOTO, TETSUO;SATO,+, J. AMER. CHEM. SOC., 112,(1990) N3, C. 5244-5252
  作者：IMAMOTO, TSUNEO、OSHIKI, TOSHIYUKI、ONOZAWA, TAKASHI、KUSUMOTO, TETSUO、SATO,+

  DOI：——

  日期：——
• Palladium catalyzed C–P cross-coupling reactions in ionic liquids
  作者：Hélène Vallette、Stéphanie Pican、Cédric Boudou、Jocelyne Levillain、Jean-Christophe Plaquevent、Annie-Claude Gaumont

  DOI：10.1016/j.tetlet.2006.05.100

  日期：2006.7

  C-P cross-coupling reactions between phosphine-borane complexes and aryl iodides are successfully performed in imidazolium based ionic liquids (ILs). To improve the recycling of the catalyst, a monophosphine covalently attached to a pyridinimn salt was prepared. Associated to palladium, this catalyst shows a high catalytic activity and stays immobilized in the IL. It was reused at least in six cycles. (c) 2006 Elsevier Ltd. All rights reserved.