α-[(pinacol)boroxy]-4-trifluoromethylbenzyl(pinacol)boronate | 910659-09-5

• 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: α-[(pinacol)boroxy]-4-trifluoromethylbenzyl(pinacol)boronate
• 英文别名: (4-CF3C6H4)CH(O(2,3-dimethyl-2,3-butanediolate))B(2,3-dimethyl-2,3-butanediolate)；(4-CF3C6H4)CH(O(pinacolate))B(pinacolate)；4,4,5,5-Tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy-[4-(trifluoromethyl)phenyl]methyl]-1,3,2-dioxaborolane
• CAS: 910659-09-5
• 化学式: C₂₀H₂₉B₂F₃O₅
• 分子量: 428.064
• InChiKey: CBXGETCWZREVAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  α-[(pinacol)boroxy]-4-trifluoromethylbenzyl(pinacol)boronate 、 氧气 生成 bis(pinacolato)diborane
  参考文献：
  名称：

  Catalytic Diboration of Aldehydes via Insertion into the Copper−Boron Bond

  摘要：

  Mesitaldehyde reacts cleanly with (IPr)CuB(pin) [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); pin = 2,3-dimethyl-2,3-butanediolate] to afford the product complex 1, the first well-defined product of carbonyl group insertion into a metal-boron bond. Analysis of 1 by NMR spectroscopy and single-crystal X-ray diffraction indicates the formation of a copper-carbon and a boron-oxygen bond. A copper(I) precatalyst supported by the less sterically demanding ligand ICy (1,3-dicyclohexylimidazol-2-ylidene) achieves the efficient 1,2-diboration of aryl-, heteroaryl-, and alkyl-substituted aldehydes at room temperature.

  DOI：

  10.1021/ja064019z
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 联硼酸频那醇酯 在 (ICy)CuOt-Bu 作用下， 以 苯 为溶剂， 反应 22.0h， 以87%的产率得到α-[(pinacol)boroxy]-4-trifluoromethylbenzyl(pinacol)boronate
  参考文献：
  名称：

  Catalytic Diboration of Aldehydes via Insertion into the Copper−Boron Bond

  摘要：

  Mesitaldehyde reacts cleanly with (IPr)CuB(pin) [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); pin = 2,3-dimethyl-2,3-butanediolate] to afford the product complex 1, the first well-defined product of carbonyl group insertion into a metal-boron bond. Analysis of 1 by NMR spectroscopy and single-crystal X-ray diffraction indicates the formation of a copper-carbon and a boron-oxygen bond. A copper(I) precatalyst supported by the less sterically demanding ligand ICy (1,3-dicyclohexylimidazol-2-ylidene) achieves the efficient 1,2-diboration of aryl-, heteroaryl-, and alkyl-substituted aldehydes at room temperature.

  DOI：

  10.1021/ja064019z

文献信息

• Catalytic Diboration of Aldehydes via Insertion into the Copper−Boron Bond
  作者：David S. Laitar、Emily Y. Tsui、Joseph P. Sadighi

  DOI：10.1021/ja064019z

  日期：2006.8.1

  Mesitaldehyde reacts cleanly with (IPr)CuB(pin) [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); pin = 2,3-dimethyl-2,3-butanediolate] to afford the product complex 1, the first well-defined product of carbonyl group insertion into a metal-boron bond. Analysis of 1 by NMR spectroscopy and single-crystal X-ray diffraction indicates the formation of a copper-carbon and a boron-oxygen bond. A copper(I) precatalyst supported by the less sterically demanding ligand ICy (1,3-dicyclohexylimidazol-2-ylidene) achieves the efficient 1,2-diboration of aryl-, heteroaryl-, and alkyl-substituted aldehydes at room temperature.