1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene tosyloxyborane | 1251715-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene tosyloxyborane
• 英文别名: [1,3-Bis[2,6-di(propan-2-yl)phenyl]imidazol-1-ium-2-yl]-(4-methylphenyl)sulfonyloxyboranuide
• CAS: 1251715-79-3
• 化学式: C₃₄H₄₅BN₂O₃S
• 分子量: 572.62
• InChiKey: GLRPPKBTAAHFKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-bis(2,6-diiopropylphenyl)imidazol-2-ylidene borane 、 对甲苯磺酸十二酯 以 甲苯 为溶剂， 以70%的产率得到1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene tosyloxyborane
  参考文献：
  名称：

  Substitution Reactions at Tetracoordinate Boron: Synthesis of N-Heterocyclic Carbene Boranes with Boron−Heteroatom Bonds

  摘要：

  Boryl halide, carboxylate and sulfonate complexes of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (dipp-Imd-BH2X, X = halide or sulfonate) have been prepared from the parent borane dipp-Imd-BH3 by (1) substitution reactions with R X (X = halide or sulfonate), (2) reactions with electrophiles (like I-2 or NIS), or (3) acid/base reactions with HX (provided that HX has a pK(a) of about 2 or less). Dipp-Imd-BH2I is most conveniently prepared by reaction with diiodine while dipp-Imd-BH2OTf is best prepared by reaction with triflic acid. These and other less reactive complexes behave as electrophiles and can be substituted by a wide range of heteroatom nucleophiles including halides, thiolates and other sulfur-based nucleophiles, isocyanate, aside, nitrite, and cyanide. The resulting products are remarkably stable, and many have been characterized by X-ray crystallography. Several are members of very rare classes of functionalized boron compounds (boron azide, nitro compound, nitrous ester, etc.).

  DOI：

  10.1021/ja107025y