2-(4-biphenyl)-4,5-dimethyl-1,3,2-dioxaborolane

• 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-(4-biphenyl)-4,5-dimethyl-1,3,2-dioxaborolane
• 英文别名: 4,5-dimethyl-2-(4′-diphenyl)-1,3,2-dioxaborolane；4,5-Dimethyl-2-(4-phenylphenyl)-1,3,2-dioxaborolane
• 化学式: C₁₆H₁₇BO₂
• 分子量: 252.121
• InChiKey: QUCGHINFBRAJGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trifluoromethyl-(4-nitrophenyl) bis(carbomethoxy)methylide 、 2-(4-biphenyl)-4,5-dimethyl-1,3,2-dioxaborolane 在 copper(l) iodide 、 1,10-菲罗啉 、 lithium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到4-三氟甲基联苯
  参考文献：
  名称：

  铜催化的（杂）芳基硼酸频哪醇酯与 YlideFluor 的三氟甲基化反应

  摘要：

  描述了铜催化的（杂）芳基硼酸频哪醇酯与 YlideFluor 的三氟甲基化反应，用于制备三氟甲基化（杂）芳烃。反应条件温和且与广泛的官能团相容。杂芳基硼酸频哪醇酯也可以高产率地进行三氟甲基化。证明了该协议在药物和 OLED 分子三氟甲基化中的应用。

  DOI：

  10.1021/acs.orglett.3c00206
• 作为产物：
  描述：

  4-溴代联苯 在 正丁基锂 、 magnesium sulfate 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 2-(4-biphenyl)-4,5-dimethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Arylation of 8-Acetoxyoctalenone in a Nickel-Catalyzed Coupling Reaction with Lithium Arylborates

  摘要：

  In order to find a suitable organometallic compound and a catalyst for the arylation of 8-acetoxyoctalenone 4 (a stereoisomeric mixture of 4 alpha and 4 beta), phenylation was first-investigated with PhZnX (7: X = Cl; 8: X = Br)/Pd or Ni cat., PhSnBu3 (9)/Pd cat. and LiCl, and [PhB(Bu)(OCHMeCHMeO)]Li (10a)/Ni cat. Berate 10a provided the desired product 11a with high stereoselectivity. The stereochemical outcome was irrespective of the stereochemistry of the acetoxy group in 4. Four more aryl groups, p-R-C6H4 (R = Me, MeO, Ph, and Me2N), were installed stereoselectively with this method.

  DOI：

  10.1002/1099-0690(200010)2000:20<3393::aid-ejoc3393>3.0.co;2-c

文献信息

• Arylation of 8-Acetoxyoctalenone in a Nickel-Catalyzed Coupling Reaction with Lithium Arylborates
  作者：Yuichi Kobayashi、Michiko Ito

  DOI：10.1002/1099-0690(200010)2000:20<3393::aid-ejoc3393>3.0.co;2-c

  日期：2000.10

  In order to find a suitable organometallic compound and a catalyst for the arylation of 8-acetoxyoctalenone 4 (a stereoisomeric mixture of 4 alpha and 4 beta), phenylation was first-investigated with PhZnX (7: X = Cl; 8: X = Br)/Pd or Ni cat., PhSnBu3 (9)/Pd cat. and LiCl, and [PhB(Bu)(OCHMeCHMeO)]Li (10a)/Ni cat. Berate 10a provided the desired product 11a with high stereoselectivity. The stereochemical outcome was irrespective of the stereochemistry of the acetoxy group in 4. Four more aryl groups, p-R-C6H4 (R = Me, MeO, Ph, and Me2N), were installed stereoselectively with this method.
• Copper-Catalyzed Trifluoromethylation of (Hetero)aryl Boronic Acid Pinacol Esters with YlideFluor
  作者：Jing Liu、Yisa Xiao、Jian Hao、Qilong Shen

  DOI：10.1021/acs.orglett.3c00206

  日期：2023.2.24

  A copper-catalyzed trifluoromethylation of (hetero)arylboronic acid pinacol esters with YlideFluor for the preparation of trifluoromethylated (hetero)arenes was described. The reaction conditions are mild and compatible with a broad range of functional groups. Heteroaryl boronic acid pinacol esters could also be trifluoromethylated in high yields. Application of this protocol for trifluoromethylation

  描述了铜催化的（杂）芳基硼酸频哪醇酯与 YlideFluor 的三氟甲基化反应，用于制备三氟甲基化（杂）芳烃。反应条件温和且与广泛的官能团相容。杂芳基硼酸频哪醇酯也可以高产率地进行三氟甲基化。证明了该协议在药物和 OLED 分子三氟甲基化中的应用。