(2-((2-methylallyl)oxy)phenyl)boronic acid | 1313761-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2-((2-methylallyl)oxy)phenyl)boronic acid
• 英文别名: [2-(2-Methylprop-2-enoxy)phenyl]boronic acid
• CAS: 1313761-30-6
• 化学式: C₁₀H₁₃BO₃
• 分子量: 192.022
• InChiKey: REXKWNPFIAUQEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-((2-methylallyl)oxy)phenyl)boronic acid 在 1,2-双(二苯基膦基)苯 、 copper(l) chloride 、 sodium t-butanolate 作用下， 以 氘代甲苯 、 甲苯 为溶剂， 反应 6.67h， 生成 甲烯丙基苯醚
  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：

  1-碘-2-((2-甲基烯丙基)氧基)苯 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 苯 为溶剂， 反应 1.5h， 以81%的产率得到(2-((2-methylallyl)oxy)phenyl)boronic acid
  参考文献：
  名称：

  Practical Radical Cyclizations with Arylboronic Acids and Trifluoroborates

  摘要：

  Practical radical cyclizations using organoboronic acids and trifluoroborates take place in water, open to air, and In a scalable fashion employing catalytic silver nitrate and stoichiometric potassium persulfate. Both Pschorr-type cyclizations and tandem radical cyclization/trap cascades are described, Illustrating the utility of these mild conditions for the generation of polycyclic scaffolds.

  DOI：

  10.1021/ol2023505

文献信息

• Apparent 6‐ <i>endo‐</i> trig Carbofluorination of Alkenes Enabled by Palladium‐Based Dyotropic Rearrangement
  作者：Jing Gong、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.202211470

  日期：2022.12.12

  cyclization mode. Pd-catalyzed cyclization of 2-(2-alkylallyloxy)phenyl boronic acid derivatives in the presence of Selectfluor 2 provides chromanes 3 with concurrent generation of a tertiary alkyl fluoride function. A 5-exo-trig carbopalladation affords PdII intermediate A whose oxidation to PdIV followed by 1,2-aryl/PdIV dyotropic rearrangement and C−F bond-forming reductive elimination affords chromane

  逆转本征环化模式。在 Selectfluor 2存在下，Pd 催化的 2-(2-烷基烯丙氧基) 苯基硼酸衍生物环化提供苯并三氢呋喃3，同时生成叔烷基氟化物功能。5 - exo -trig carbopalladation 提供 Pd II中间体A，其氧化为 Pd IV，然后进行 1,2-芳基/Pd IV变色重排和 C−F 键形成还原消除，得到苯并三氢呋喃3。
• Copper-Catalyzed Regio- and Stereoselective Intermolecular Three-Component Oxyarylation of Allenes
  作者：Taisuke Itoh、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/ol501022d

  日期：2014.5.16

  A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereo-selectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.
• Practical Radical Cyclizations with Arylboronic Acids and Trifluoroborates
  作者：Jonathan W. Lockner、Darryl D. Dixon、Rune Risgaard、Phil S. Baran

  DOI：10.1021/ol2023505

  日期：2011.10.21

  Practical radical cyclizations using organoboronic acids and trifluoroborates take place in water, open to air, and In a scalable fashion employing catalytic silver nitrate and stoichiometric potassium persulfate. Both Pschorr-type cyclizations and tandem radical cyclization/trap cascades are described, Illustrating the utility of these mild conditions for the generation of polycyclic scaffolds.
• 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.