4,4,5,5-tetramethyl-2-(2-((2-methylallyl)oxy)phenyl)-1,3,2-dioxaborolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,4,5,5-tetramethyl-2-(2-((2-methylallyl)oxy)phenyl)-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-Tetramethyl-2-[2-(2-methylprop-2-enoxy)phenyl]-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-[2-(2-methylprop-2-enoxy)phenyl]-1,3,2-dioxaborolane
• 化学式: C₁₆H₂₃BO₃
• 分子量: 274.168
• InChiKey: BFPKKNOFBLFQJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4,5,5-tetramethyl-2-(2-((2-methylallyl)oxy)phenyl)-1,3,2-dioxaborolane 在 1,2-双(二苯基膦基)苯 、 copper(l) chloride 、 sodium t-butanolate 、 氘代甲醇 作用下， 以 氘代甲苯 为溶剂， 反应 4.17h， 以96%的产率得到
  参考文献：
  名称：

  Diarylation of Alkenes by a Cu-Catalyzed Migratory Insertion/Cross-Coupling Cascade

  摘要：

  A strategy for the catalytic diarylation of alkenes is presented. The method involves the migratory insertion of alkenes into an Ar-Cu complex to generate a new C(sp(3))-Cu complex, which subsequently undergoes reaction with an aryl iodide to constitute a vicinal diarylation of an alkene. The method provides access to benzofuran- and indoline-containing products. Furthermore, highly diastereoselective examples are presented, allowing access to complex, stereochemically rich structures from simple alkene starting materials.

  DOI：

  10.1021/ja509056j
• 作为产物：
  描述：

  频哪醇 、 (2-((2-methylallyl)oxy)phenyl)boronic acid 以 甲苯 为溶剂， 反应 1.0h， 以89%的产率得到4,4,5,5-tetramethyl-2-(2-((2-methylallyl)oxy)phenyl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  Diarylation of Alkenes by a Cu-Catalyzed Migratory Insertion/Cross-Coupling Cascade

  摘要：

  A strategy for the catalytic diarylation of alkenes is presented. The method involves the migratory insertion of alkenes into an Ar-Cu complex to generate a new C(sp(3))-Cu complex, which subsequently undergoes reaction with an aryl iodide to constitute a vicinal diarylation of an alkene. The method provides access to benzofuran- and indoline-containing products. Furthermore, highly diastereoselective examples are presented, allowing access to complex, stereochemically rich structures from simple alkene starting materials.

  DOI：

  10.1021/ja509056j

文献信息

• Catalytic Enantioselective Diarylation of Alkenes
  作者：Wei You、M. Kevin Brown

  DOI：10.1021/jacs.5b10176

  日期：2015.11.25

  for the catalytic enantioselective diarylation of alkenes is presented. The method allowed for the synthesis of highly enantioenriched 2,3-dihydrobenzofurans and indolines containing molecules from readily available substrates. Furthermore, this method allowed for the enantioselective synthesis of quaternary carbons. Based on mechanism studies, the process likely functions by enantioselective insertion

  提出了一种烯烃催化对映选择性二芳基化的方法。该方法允许从容易获得的底物合成含有高度对映体的 2,3-二氢苯并呋喃和二氢吲哚分子。此外，该方法允许对映选择性合成季碳。根据机理研究，该过程可能通过将烯烃对映选择性插入 Ar-CuBenzP* 复合物以生成 Csp(3)-Cu 复合物来发挥作用。用 ArX 捕获该中间体导致形成所需产物。
• Diarylation of Alkenes by a Cu-Catalyzed Migratory Insertion/Cross-Coupling Cascade
  作者：Wei You、M. Kevin Brown

  DOI：10.1021/ja509056j

  日期：2014.10.22

  A strategy for the catalytic diarylation of alkenes is presented. The method involves the migratory insertion of alkenes into an Ar-Cu complex to generate a new C(sp(3))-Cu complex, which subsequently undergoes reaction with an aryl iodide to constitute a vicinal diarylation of an alkene. The method provides access to benzofuran- and indoline-containing products. Furthermore, highly diastereoselective examples are presented, allowing access to complex, stereochemically rich structures from simple alkene starting materials.