methyldiphenylsilyl iodide

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: methyldiphenylsilyl iodide
• 英文别名: Iodo-methyl-diphenylsilane
• 化学式: C₁₃H₁₃ISi
• 分子量: 324.236
• InChiKey: BVNUCMYKVJKWNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  methyldiphenylsilyl iodide 以 various solvent(s) 为溶剂， 以52%的产率得到1,2-二甲基-1,1,2,2-四苯基乙硅烷
  参考文献：
  名称：

  Electrolytic Behavior of Iodo- and Chlorosilanes. The Formation of Si-Si and Si-sp-C Bonds

  摘要：

  用铝/铂电极在戊腈中进行碘硅烷的电解会生成硅-硅键，从而形成相应的二硅烷。另一方面，在酚乙炔存在下，用铂/铂电极电解各种卤硅烷，如碘硅烷、氯硅烷和氟硅烷，会生成硅-碳三键，从而得到苯乙炔衍生物。

  DOI：

  10.1246/cl.1995.1051
• 作为产物：
  描述：

  二苯甲基硅烷 在 palladium dichloride 、 碘甲烷 作用下， 反应 18.5h， 以88%的产率得到methyldiphenylsilyl iodide
  参考文献：
  名称：

  钯催化的甲硅烷基亲电试剂与烷基卤化锌的交叉偶联：甲硅烷基-根岸反应

  摘要：

  我们报告了二级锌有机金属和硅亲电试剂之间甲硅烷基-Negishi 反应的第一个例子。这种钯催化工艺可直接获得烷基硅烷。所用 DrewPhos 配体的空间和电子参数的微妙平衡对于抑制异构化和促进有效和选择性的交叉偶联至关重要。

  DOI：

  10.1021/jacs.7b04364

文献信息

• A Bench-Stable, Single-Component Precatalyst for Silyl–Heck Reactions
  作者：Sarah B. Krause、Jesse R. McAtee、Glenn P. A. Yap、Donald A. Watson

  DOI：10.1021/acs.orglett.7b02807

  日期：2017.10.20

  reaction aimed at identifying active palladium complexes have revealed a new species that is formed in situ. This complex has been identified as the palladium iodide dimer, [(JessePhos)PdI2]2, which has been found to be a competent single-component precatalyst for the silyl-Heck reaction. This complex is easily prepared and is temperature, moisture, and air stable. Additionally, this precatalyst provides

  旨在鉴定活性钯配合物的甲硅烷基-Heck反应的研究揭示了一种原位形成的新物种。该络合物已被鉴定为碘化钯二聚体[（JessePhos）PdI 2 ] 2，已发现它是甲硅烷基-Heck反应的有效单组分预催化剂。该配合物易于制备，并且对温度，湿度和空气稳定。另外，与以前的系统相比，这种预催化剂具有更高的活性和更高的重现性。
• Selective synthesis of halosilanes from hydrosilanes and utilization for organic synthesis
  作者：Atsutaka Kunai、Joji Ohshita

  DOI：10.1016/s0022-328x(03)00254-7

  日期：2003.11

  Selective synthesis of halosilanes has been examined. Various types of halosilanes and halohydrosilanes, such as R3SiX, R2SiHX, R2SiX2, RSiH2X, RSiHX2 (X = Cl, Br, F), were obtained by the reactions of the corresponding hydrosilanes with Cu(II)-based reagents selectively in high yields. This method could be also applied to the synthesis of chlorofluorosilanes and chlorohydrogermanes. On the other hand, iodo- and bromosilanes and germanes were obtained by Pd- or Ni-catalyzed hydride-halogen exchange reactions of hydrosilanes with alkyl or allyl halides. Their synthetic applications have been demonstrated by using iodo-and bromosilanes and chlorofluorosilanes. (C) 2003 Elsevier Science B.V. All rights reserved.
• Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction
  作者：Andrew P. Cinderella、Bojan Vulovic、Donald A. Watson

  DOI：10.1021/jacs.7b04364

  日期：2017.6.14

  the first example of a silyl-Negishi reaction between secondary zinc organometallics and silicon electrophiles. This palladium-catalyzed process provides direct access to alkyl silanes. The delicate balance of steric and electronic parameters of the employed DrewPhos ligand is paramount to suppressing isomerization and promoting efficient and selective cross-coupling.

  我们报告了二级锌有机金属和硅亲电试剂之间甲硅烷基-Negishi 反应的第一个例子。这种钯催化工艺可直接获得烷基硅烷。所用 DrewPhos 配体的空间和电子参数的微妙平衡对于抑制异构化和促进有效和选择性的交叉偶联至关重要。
• Electrolytic Behavior of Iodo- and Chlorosilanes. The Formation of Si-Si and Si-<i>sp</i>-C Bonds
  作者：Atsutaka Kunai、Osamu Ohnishi、Tomohiro Sakurai、Mitsuo Ishikawa

  DOI：10.1246/cl.1995.1051

  日期：1995.11

  Electrolysis of iodosilanes with Al/Pt electrodes in pivalonitrile results in the formation of the Si–Si bonds to give the corresponding disilanes. On the other hand, the electrolysis of various halosilanes such as iodo-, chloro-, and fluorosilanes with Pt/Pt electrodes in the presence of phenylacetylene leads to the formation of the Si–sp-carbon bonds to give phenylethynylated products.

  用铝/铂电极在戊腈中进行碘硅烷的电解会生成硅-硅键，从而形成相应的二硅烷。另一方面，在酚乙炔存在下，用铂/铂电极电解各种卤硅烷，如碘硅烷、氯硅烷和氟硅烷，会生成硅-碳三键，从而得到苯乙炔衍生物。