benzylmanganese(II) chloride | 180069-62-9

• 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: benzylmanganese(II) chloride
• 英文别名: benzylmanganese chloride
• CAS: 180069-62-9
• 化学式: C₇H₇ClMn
• 分子量: 181.524
• InChiKey: CGOQFWDYKCPJBE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 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：

  (1E)-3-甲基-1-硝基-1-丁烯 、 benzylmanganese(II) chloride 以 四氢呋喃 为溶剂， 以73%的产率得到[3-Methyl-2-(nitromethyl)butyl]benzene
  参考文献：
  名称：

  Additions of organomanganese reagents to conjugated nitroolefins

  摘要：

  Additions of organomanganese reagents to aromatic and aliphatic conjugated nitroolefins were examined for the first time. In most cases reaction proceeded rapidly at -30 degrees C. Unlike Mn reagents lacking beta-hydrogens (Me, Ph), which lead to oxidative coupling and reductive dimerisation of nitrostyrenes, benzylmanganese chloride gives 1,4-addition in yields exceeding Grignard or Cu-assisted additions. At 0 degrees C alkyl(Bu, Pr)-manganese reagents undergo an addition-migration-elimination process with nitrostyrenes providing a convenient and stereospecific entry into arylated trans-olefins.

  DOI：

  10.1016/0022-328x(96)06150-5
• 作为产物：
  描述：

  lithium manganese chloride 、 氯化苄 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到benzylmanganese(II) chloride
  参考文献：
  名称：

  镍催化的功能化有机锰试剂与4-氟苯乙烯促进的芳基和杂芳基卤化物的交叉偶联

  摘要：

  摘要 由Ni（acac）2（5 mol％）和4-氟苯乙烯（20 mol％）组成的催化系统可以方便地将官能化的有机锰试剂与各种芳基和杂芳基卤化物交叉偶联，从而得到多官能化的二芳基和芳基杂芳基甲烷衍生物。 由Ni（acac）2（5 mol％）和4-氟苯乙烯（20 mol％）组成的催化系统可以方便地将官能化的有机锰试剂与各种芳基和杂芳基卤化物交叉偶联，从而得到多官能化的二芳基和芳基杂芳基甲烷衍生物。

  DOI：

  10.1055/s-0036-1589101

文献信息

• Direct preparation of benzylic manganese reagents from benzyl halides, sulfonates, and phosphates and their reactions: applications in organic synthesis
  作者：YoungSung Suh、Jun-sik Lee、Seoung-Hoi Kim、Reuben D Rieke

  DOI：10.1016/s0022-328x(03)00500-x

  日期：2003.11

  The use of highly active manganese (Mn)*, prepared by the Rieke method, was investigated for the direct preparation of benzylic manganese reagents. The oxidative addition of the highly active manganese to benzylic halides was easily completed under mild conditions. Moreover, benzylic manganese sulfonates and phosphates were prepared by direct oxidative addition of Mn* to the carbon–oxygen bonds of

  研究了通过Rieke方法制备的高活性锰（Mn）*用于直接制备苄基锰试剂的方法。高活性锰在苄基卤化物中的氧化加成反应很容易在温和的条件下完成。此外，通过将Mn *直接氧化加成到苄基磺酸盐和磷酸盐的碳-氧键上来制备苄基锰磺酸盐和磷酸盐。发现所得的苄基锰试剂与多种亲电试剂发生交叉偶联反应。这些反应大多数在温和条件下在不存在任何过渡金属催化剂的情况下进行。此外，还研究了使用高活性锰制备不含过渡金属催化剂的功能化苄基卤化物的均偶联产物。N-烷氧基羰基吡啶鎓盐。
• Iron-Catalyzed Cross-Coupling of Benzylic Manganese Chlorides with Aryl and Heteroaryl Halides
  作者：Paul Knochel、Andreas Benischke、Antoine Breuillac、Alban Moyeux、Gérard Cahiez

  DOI：10.1055/s-0035-1560812

  日期：——

  The use of FeCl2 (10 mol%) allows a convenient iron-catalyzed cross-coupling reaction of benzylic manganese(II) chlorides with various aryl and heteroaryl chlorides, bromides and iodides leading to polyfunctionalized diaryl- and arylheteroarylmethane derivatives.

  FeCl2 (10 mol%) 的使用允许苄基氯化锰 (II) 与各种芳基和杂芳基氯化物、溴化物和碘化物进行方便的铁催化交叉偶联反应，产生多官能化的二芳基和芳基杂芳基甲烷衍生物。
• Versatile palladium-catalyzed arylation of organomanganese chlorides by aryl bromides
  作者：Eric Riguet、Mouâd Alami、Gérard Cahiez

  DOI：10.1016/s0022-328x(00)00891-3

  日期：2001.4

  In THF, a palladium-catalyzed cross-coupling reaction of organomanganese reagents with various aryl bromides including unreactive deactivated or hindered aryl bromides was performed successfully in the presence of a new catalytic system 1% PdCl2(dppp)-four equivalents DME. The scope of the reaction is very broad since many functional groups are tolerated, moreover, even hindered O,O ' -di- or trisubstituted diaryls were obtained in E;igh yields. It is interesting to note that hindered aryl bromides are more reactive than the corresponding aryl iodides. Alkyl, alkenyl and alkynylmanganese chlorides also react under similar conditions. (C) 2001 Elsevier Science B.V. All rights reserved.