(1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate | 1251715-87-3

• 英文名称: (1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate
• 英文别名: 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene (phenylthio)borane
• CAS: 1251715-87-3
• 化学式: C₃₃H₄₃BN₂S
• 分子量: 510.595
• InChiKey: NEQWRMJVAOEMCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene (trifluoromethylsulfonyloxy)borane 、 苯硫酚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 氘代氯仿 为溶剂， 反应 24.0h， 以58%的产率得到(1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate
  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

文献信息

• Mechanistic and Preparative Studies of Radical Chain Homolytic Substitution Reactions of N-Heterocyclic Carbene Boranes and Disulfides
  作者：Xiangcheng Pan、Anne-Laure Vallet、Stéphane Schweizer、Karim Dahbi、Bernard Delpech、Nicolas Blanchard、Bernadette Graff、Steven J. Geib、Dennis P. Curran、Jacques Lalevée、Emmanuel Lacôte

  DOI：10.1021/ja403627k

  日期：2013.7.17

  Reactions of 1,3-dimethylimidazol-2-ylidene-borane (diMe-Imd-BH3) and related NHC-boranes with diaryl and diheteroaryl disulfides provide diverse NHC-boryl monosulfides (diMe-Imd-BH2SAr) and NHC-boryl disulfides (diMe-Imd-BH(SAr)2). Heating in the dark with 1 equiv of disulfide favors monosulfide formation, while irradiation with 2 equiv disulfide favors disulfide formation. With heteroaryl disulfides

  1,3-二甲基咪唑-2-亚基-硼烷 (diMe-Imd-BH3) 和相关的 NHC-硼烷与二芳基和二杂芳基二硫化物的反应提供了多种 NHC-硼基单硫化物 (diMe-Imd-BH2SAr) 和 NHC-硼基二硫化物 (diMe -Imd-BH(SAr)2)。在黑暗中用 1 当量二硫化物加热有利于单硫化物的形成，而用 2 当量二硫化物照射有利于二硫化物的形成。对于杂芳基二硫化物，主要 NHC-硼基硫化物产品中的 NHC-硼烷从硫迁移到氮，得到具有硫代酰胺亚结构的新产品。大多数取代反应被认为是通过自由基链进行的，其中 NHC-硼基自由基对二硫化物的均裂取代是关键步骤。然而，对于黑暗条件下的亲电二硫化物，竞争性离子路径也可能是可能的。