2,2-dimethyl-7-phenyl-3H-1-benzofuran | 1286763-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,2-dimethyl-7-phenyl-3H-1-benzofuran
• CAS: 1286763-02-7
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: JFRIELOGAMYJGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  呋喃酚 在 potassium phosphate 、 二氯化双(三环己基膦)镍(II) 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 41.0h， 生成 2,2-dimethyl-7-phenyl-3H-1-benzofuran
  参考文献：
  名称：

  Suzuki−Miyaura Cross-Coupling of Aryl Carbamates and Sulfamates: Experimental and Computational Studies

  摘要：

  The first Suzuki-Miyaura cross-coupling reactions of the synthetically versatile aryl O-carbamate and O-sulfamate groups are described. The transformations utilize the inexpensive, bench-stable catalyst NiCl2(PCy3)(2) to furnish biaryls in good to excellent yields. A broad scope for this methodology has been demonstrated. Substrates with electron-donating and electron-withdrawing groups are tolerated, in addition to those that possess ortho substituents. Furthermore, heteroaryl substrates may be employed as coupling partners. A computational study providing the full catalytic cycles for these cross-coupling reactions is described. The oxidative addition with carbamates or sulfamates occurs via a five-centered transition state, resulting in the exclusive cleavage of the aryl C-O bond. Water is found to stabilize the Ni-carbamate catalyst resting state, which thus provides rationalization of the relative decreased rate of coupling of carbamates. Several synthetic applications are presented to showcase the utility of the methodology in the synthesis of polysubstituted aromatic compounds of natural product and bioactive molecule interest.

  DOI：

  10.1021/ja200398c

文献信息

• Nickel-Catalyzed Suzuki–Miyaura Couplings in Green Solvents
  作者：Stephen D. Ramgren、Liana Hie、Yuxuan Ye、Neil K. Garg

  DOI：10.1021/ol401727y

  日期：2013.8.2

  The nickel-catalyzed Suzuki-Miyaura coupling of aryl halides and phenol-derived substrates with aryl boronic acids using green solvents, such as 2-Me-THF and tert-amyl alcohol, is reported. This methodology employs the commercially available and air-stable precatalyst, NiCl2(PCy3)(2), and gives biaryl products in synthetically useful to excellent yields. Using this protocol, bis(heterocyclic) frameworks can be assembled efficiently.