(2,2-diphenylethyl)diphenylsilane | 1378240-68-6

• 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: (2,2-diphenylethyl)diphenylsilane
• 英文别名: 2,2-diphenylethyl(diphenyl)silane
• CAS: 1378240-68-6
• 化学式: C₂₆H₂₄Si
• 分子量: 364.562
• InChiKey: VJSIWSZGIJWOPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  (2,2-diphenylethyl)diphenylsilane 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 norbornene 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以76%的产率得到1,1,3-triphenyl-2,3-dihydro-1H-benzo[b]silole
  参考文献：
  名称：

  General and Practical One-Pot Synthesis of Dihydrobenzosiloles from Styrenes

  摘要：

  A one-pot synthesis of dihydrobenzosiloles from styrenes has been developed. The reaction involves the nickel-catalyzed hydrosilylation of styrene with diphenylsilane, followed by the iridium-catalyzed dehydrogenative cyclization. This method is efficient for both electron-rich and -deficient styrenes and exhibits good functional group tolerance, as well as excellent regioselectivity. The forming dihydrobenzosiloles can be efficiently converted into valuable benzosiloles or 2-hydroxyphenethyl alcohols.

  DOI：

  10.1021/ol203428c
• 作为产物：
  描述：

  1,1-二苯乙烯 、 二苯基硅烷 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到(2,2-diphenylethyl)diphenylsilane
  参考文献：
  名称：

  Alkene hydrosilylation catalyzed by easily assembled Ni(ii)-carboxylate MOFs

  摘要：

  易于组装的Ni MOFs对烯烃氢硅烷化反应具有高效和稳健的催化作用。

  DOI：

  10.1039/c9sc00126c

文献信息

• Cationic Nickel(II)-Catalyzed Hydrosilylation of Alkenes: Role of P, N-Type Ligand Scaffold on Selectivity and Reactivity
  作者：Istiak Hossain、Joseph A. R. Schmidt

  DOI：10.1021/acs.organomet.0c00551

  日期：2020.9.28

  Seven structurally similar cationic nickel(II)–alkyl complexes were synthesized by using a series of P, N ligands, and their reactivity was explored in the hydrosilylation of alkenes. More electron-rich phosphines enhanced the overall reactivity of the transformation; in contrast, groups on the imine donor had little impact. Overall, these catalysts displayed reactivity and selectivity that was previously

  使用一系列P，N配体合成了七个结构相似的阳离子镍（II）-烷基络合物，并在烯烃的氢硅烷化中探索了它们的反应性。更多的富电子膦提高了转化的整体反应性；相反，亚胺供体上的组几乎没有影响。总体而言，这些催化剂显示出在镍催化的氢化硅烷化中以前未知或非常罕见的反应性和选择性。在与Ph 2 SiH 2的反应中，1,2-二取代的乙烯基芳烃显示出对硅烷加成的完全苄基选择性，而对1,1-二取代的烯烃则观察到末端选择性。相关的PhSiH 3导致仅对单个取代的乙烯基芳烃进行马尔可夫尼科夫选择性，而未观察到竞争的双加成。机理研究支持以下假设：Ni-H在此催化氢硅烷化反应中充当活性物质，这反过来也显示了硅烷再分布反应的催化能力，特别是对于空间不受阻的硅烷。
• B(C₆F₅)₃-Catalyzed Synthesis of Benzofused-Siloles
  作者：Liam D. Curless、Michael J. Ingleson

  DOI：10.1021/om501033p

  日期：2014.12.22

  a weak base forms silafluorenes with H2 as the only byproduct. Attempts to extend this approach to synthesize siloles derived from 2,2′-bithiophenes and N-Me-2-Ph-indole resulted in competing reactivity, including protodesilylation. B(C6F5)3 also catalyzed the one-pot, two-step formation of silaindenes from aryl-alkynes by alkyne trans-hydrosilylation, followed by an intramolecular Sila-Friedel–Crafts

  由B（C 6 F 5）3和弱碱催化的2-（SiR 2 H）-联苯的脱氢硅烷化反应形成了以H 2为唯一副产物的硅芴。尝试将该方法扩展为合成由2,2'-联噻吩和N -Me-2-Ph-吲哚衍生的甲硅烷导致竞争的反应性，包括原去甲硅烷基化。B（C 6 F 5）3还催化了炔烃的反式氢化硅烷化作用，由芳基炔烃一锅，两步形成硅氢化茚，然后通过弱碱促进了分子内Sila-Friedel-Crafts反应。
• Hydrosilylation catalysis by an earth alkaline metal silyl: synthesis, characterization, and reactivity of bis(triphenylsilyl)calcium
  作者：Valeri Leich、Thomas P. Spaniol、Laurent Maron、Jun Okuda

  DOI：10.1039/c3cc49308c

  日期：——

  Bis(triphenylsilyl)calcium [Ca(SiPh3)2(thf)] obtained in high yield as a crystalline ether adduct catalyzes the hydrosilylation of activated C-C double bonds efficiently and regioselectively.

  以结晶醚加合物形式高收率获得的双（三苯基甲硅烷基）钙[Ca（SiPh3）2（thf）]有效且区域选择性地催化了活化CC双键的氢化硅烷化。
• Anti-Markovnikov terminal and <i>gem</i>-olefin hydrosilylation using a κ⁴-diimine nickel catalyst: selectivity for alkene hydrosilylation over ether C–O bond cleavage
  作者：Christopher L. Rock、Ryan J. Trovitch

  DOI：10.1039/c8dt04608e

  日期：——

  found to catalyze alkene hydrosilylation in the presence of Ph2SiH2 with turnover frequencies of up to 124 h−1 at 25 °C (990 h−1 at 60 °C). Moreover, the selective hydrosilylation of allylic and vinylic ethers has been demonstrated, even though (Ph2PPrDI)Ni is known to catalyze allyl ester C–O bond hydrosilylation. At 70 °C, this catalyst has been found to mediate the hydrosilylation of ten different

  已发现，在25°C（990 h时，Ph 2 SiH 2存在下，膦取代的α-二亚胺Ni前体（Ph 2 PPr DI）Ni可以催化烯烃氢化硅烷化，其转换频率高达124 h -1 -1在60°C时）。此外，即使已知（Ph 2 PPr DI）Ni可以催化烯丙基酯C–O键的氢化硅烷化反应，也证明了烯丙基和乙烯基醚的选择性氢化硅烷化反应。在70°C下，已发现该催化剂可介导十种不同宝石的氢化硅烷化-烯烃，在纯净条件下的营业额高达740。先前和当前的机械观察结果表明，在膦供体解离后，烯烃的氢化硅烷化是通过Chalk-Harrod机理进行的。
• Hypervalent Hydrosilicates Connected to Light Alkali Metal Amides: Synthesis, Structure, and Hydrosilylation Catalysis
  作者：Danny Schuhknecht、Valeri Leich、Thomas P. Spaniol、Jun Okuda

  DOI：10.1002/chem.201803373

  日期：2018.9.12

  When light alkali metal amides [M(Me3TACD)]n (M=Li, Na, K; (Me3TACD)H=1,4,7‐trimethyl‐1,4,7,10‐tetraazacyclododecane) were treated with H2SiPh2 in THF, [M(H2SiPh2)Me3TACD}(thf)x] containing a pendant hypervalent dihydridosilicate were formed and characterized by elemental analysis, NMR/IR spectroscopy, and single‐crystal X‐ray crystallography. The lithium complex catalyzed the hydrosilylation of styrene

  处理轻碱金属酰胺[M（Me 3 TACD）] n（M = Li，Na，K;（Me 3 TACD）H = 1,4,7-三甲基-1,4,7,10-四氮杂环十二烷）用THF中的H 2 SiPh 2形成了[M （H 2 SiPh 2）Me 3 TACD}（thf）x ]，它含有侧链超价二氢硅酸盐，并通过元素分析，NMR / IR光谱和单晶X-进行了表征射线晶体学。锂络合物在温和条件下以反马尔科夫尼科夫区域选择性催化苯乙烯衍生物的氢化硅烷化。