triethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane | 1554400-95-1

• 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: triethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane
• 英文别名: Triethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]silane
• CAS: 1554400-95-1
• 化学式: C₁₈H₃₁BO₂Si
• 分子量: 318.339
• InChiKey: XWXDQCVVGMDUPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  六乙基乙硅烷 在 copper(l) iodide 、 四甲基乙二胺 、 三丁基膦 、 4,4-二苯基-2,2-二联吡啶 、 三(N,N-四亚甲基)磷酰胺 、 potassium tert-butylate 、 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.08h， 生成 triethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane
  参考文献：
  名称：

  Copper-catalyzed silylation of aryl and alkenyl triflates with silylboronic esters avoiding base-mediated borylation

  摘要：

  Catalytic silylation of aryl/alkenyl electrophiles using silylboronic esters with no base-mediated borylation has been developed.

  DOI：

  10.1039/d4cc01005a

文献信息

• Construction of C(sp²)–Si Bonds via Ligand-Promoted C–C Bonds Cleavage of Unstrained Ketones
  作者：Xing Wang、Zhen-Yu Wang、Xu Zhang、Hui Xu、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.2c02841

  日期：2022.10.14

  Herein, we report an efficient palladium-catalyzed silylation of aryl and alkenyl ketones via C–C bond cleavage and C–Si bond formation. This protocol features high efficiency and broad substrate scope. Further applications in the late-stage diversification of biologically important molecules demonstrate the synthetic utility of this method.

  在此，我们报道了通过 C-C 键断裂和 C-Si 键形成有效的钯催化的芳基和烯基酮的硅烷化。该协议具有高效率和广泛的基板范围。在生物重要分子的后期多样化中的进一步应用证明了这种方法的综合效用。
• A Mild Ni/Cu-Catalyzed Silylation via C<i>–</i>O Cleavage
  作者：Cayetana Zarate、Ruben Martin

  DOI：10.1021/ja412107b

  日期：2014.2.12

  A Ni/Cu-catalyzed silylation of unactivated C-O electrophiles derived from phenols or benzyl alcohols is described. This transformation is characterized by its wide scope and mild conditions, providing a direct access to synthetically versatile silylated compounds. The protocol allows for the coupling of C(sp(2))-O and even C(sp(3))-O bonds with similar efficiency.
• <i>para</i>-C–H Borylation of Benzene Derivatives by a Bulky Iridium Catalyst
  作者：Yutaro Saito、Yasutomo Segawa、Kenichiro Itami

  DOI：10.1021/jacs.5b02052

  日期：2015.4.22

  A highly para-selective aromatic C-H borylation has been accomplished. By a new iridium catalyst bearing a bulky diphosphine ligand, Xyl-MeO-BIPHEP, the C-H borylation of monosubstituted benzenes can be affected with para-selectivity up to 91%. This catalytic system is quite different from the usual iridium catalysts that cannot distinguish meta- and para-C-H bonds of monosubstituted benzene derivatives, resulting in the preferred formation of meta-products. The para-selectivity increases with increasing bulkiness of the substituent on the arene, indicating that the regioselectivity of the present reaction is primarily controlled by steric repulsion between substrate and catalyst. Caramiphen, an anticholinergic drug used in the treatment of Parkinsons disease, was converted into five derivatives via our para-selective borylation. The present [Ir(cod)OH](2)/Xyl-MeO-BIPHEP catalyst represents a unique, sterically controlled, para-selective, aromatic C-H borylation system that should find use in streamlined, predictable chemical synthesis and in the rapid discovery and optimization of pharmaceuticals and materials.