反式双（二环己基苯基膦基）氯化镍（II）

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 反式双（二环己基苯基膦基）氯化镍（II）
• 英文名称: bis(dicyclohexylphenylphosphine)nickel(II) chloride
• 英文别名: NiCl2(phenyldi(cyclohexyl)phosphine)2；[NiCl2(P(phenyl)(cyclohexyl)2)2]；Ni(Cy2PhP)2Cl2；Nickel(2+) bis(dicyclohexylphenylphosphine) dichloride；dicyclohexyl(phenyl)phosphane;nickel(2+);dichloride
• 化学式: C₃₆H₅₄Cl₂NiP₂
• 分子量: 678.368
• InChiKey: GFEHDJMDCSIPBL-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  12.29
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  sodium 、 反式双（二环己基苯基膦基）氯化镍（II） 在 CO 作用下， 以 甲苯 为溶剂， 以74%的产率得到bis(dicyclohexylphenylphosphine)dicarbonylnickel
  参考文献：
  名称：

  Dicyclohexylphosphido complexes of nickel(I)

  摘要：

  DOI：

  10.1016/s0020-1693(00)90101-4
• 作为产物：
  描述：

  氯代环己烷 以 乙醚 、 乙醇 为溶剂， 反应 2.5h， 生成 反式双（二环己基苯基膦基）氯化镍（II）
  参考文献：
  名称：

  Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes

  摘要：

  The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy2Ph)(2)Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki-Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.

  DOI：

  10.1021/ja3116718
• 作为试剂：
  描述：

  phenylmagnesium bromide 、 4-甲氧基苯酚 在 反式双（二环己基苯基膦基）氯化镍（II） 作用下， 以 various solvent(s) 为溶剂， 反应 15.0h， 生成 对羟基联苯
  参考文献：
  名称：

  镍催化的芳基格氏试剂与芳族烷基醚的交叉偶联：不对称联芳基的有效合成。

  摘要：

  DOI：

  10.1002/anie.200453765

文献信息

• A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes
  作者：Eric A. Standley、Stacey J. Smith、Peter Müller、Timothy F. Jamison

  DOI：10.1021/om500156q

  日期：2014.4.28

  A series of air-stable nickel complexes of the form L2Ni(aryl) X (L = monodentate phosphine, X = Cl, Br) and LNi(aryl)X (L = bis-phosphine) have been synthesized and are presented as a library of precatalysts suitable for a wide variety of nickel-catalyzed transformations. These complexes are easily synthesized from low-cost NiCl2·6H2O or NiBr2·3H2O and the desired ligand followed by addition of 1

  已经合成了一系列 L 2 Ni（芳基）X（L = 单齿膦，X = Cl，Br）和 LNi（芳基）X（L = 双膦）形式的空气稳定镍配合物，并表示为适用于各种镍催化转化的预催化剂库。这些配合物很容易由低成本的 NiCl 2 ·6H 2 O 或 NiBr 2 ·3H 2合成O 和所需的配体，然后加入 1 当量的格氏试剂。选择的这些配合物通过单晶 X 射线衍射进行了表征，并提供了对其结构特征的分析。介绍了将它们用作镍催化羰基-烯反应的预催化剂的案例研究，与使用 Ni(cod) 2 的反应相比，显示出优异的反应性。此外，由于预催化剂都对空气稳定，因此不需要手套箱或惰性气氛技术来利用这些配合物进行镍催化反应。
• [EN] NICKEL PRE-CATALYSTS AND RELATED COMPOSITIONS AND METHODS<br/>[FR] PRÉ-CATALYSEURS DE NICKEL ET COMPOSITIONS ET MÉTHODES ASSOCIÉES
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2015070026A1

  公开（公告）日：2015-05-14

  Described herein are nickel pre-catalysts and related compositions and methods. The nickel pre-catalysts may be activated to form catalysts which may be utilized in organic reactions.

  本文描述了镍前催化剂及相关组成物和方法。这些镍前催化剂可以被活化形成催化剂，可用于有机反应中。
• Bench-Stable Nickel Precatalysts with Heck-type Activation
  作者：Jessica M. Weber、Ashley R. Longstreet、Timothy F. Jamison

  DOI：10.1021/acs.organomet.8b00351

  日期：2018.8.27

  synthesis and characterization of a new class of air- and moisture-stable phosphine-containing nickel(II) precatalysts, which activate through a Heck-type mechanism. The activities of the precatalysts are demonstrated with a carbonyl-ene coupling reaction.

  本文中，我们报告了一种新型的空气和水分稳定的含膦膦镍（II）预催化剂的合成和表征，该催化剂通过Heck型机理活化。通过羰基-烯偶联反应证明了预催化剂的活性。
• Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes
  作者：Eric A. Standley、Timothy F. Jamison

  DOI：10.1021/ja3116718

  日期：2013.1.30

  The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy2Ph)(2)Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki-Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.
• Dicyclohexylphosphido complexes of nickel(I)
  作者：C.F. Nobile、G. Vasapollo、P. Giannoccaro、A. Sacco

  DOI：10.1016/s0020-1693(00)90101-4

  日期：1981.1