(1,3-diisopropyl-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate | 1338729-09-1

• 英文名称: (1,3-diisopropyl-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate
• 英文别名: 1,3-diisopropylimidazol-2-ylidene (phenylthio)borane
• CAS: 1338729-09-1
• 化学式: C₁₅H₂₃BN₂S
• 分子量: 274.238
• InChiKey: FRISZANLDDIUDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 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：
  None

反应信息

• 作为产物：
  描述：

  1,3-diisopropylimidazol-2-ylidene borane 、 二苯二硫醚 以66%的产率得到(1,3-diisopropyl-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate
  参考文献：
  名称：

  N-杂环碳烯·硼烷可自由基还原卤代物时，二硫化物和硼烷基硫化物既是引发剂又是前催化剂

  摘要：

  AbstractDiphenyl disulfide (PhSSPh), a typical boryl monosulfide (diiPr‐Imd‐BH2SPh) and a typical boryl bis‐sulfide [diMe‐Imd‐BH(SPh)2] all serve as both initiators and precatalysts in the reduction of alkyl and aryl halides by readily available 1,3‐dimethylimidazol‐2‐ylidene⋅borane (diMe‐Imd‐BH3). The reactions are suggested to occur by a polarity reverse catalysis mechanism where in situ generated thiophenol is the active catalyst.magnified image

  DOI：

  10.1002/adsc.201300752
• 作为试剂：
  描述：

  N-allyl-N-(2-bromoethyl)-4-methylbenzenesulfonamide 在 (1,3-dimethylimidazol-2-ylidene)borane 、 (1,3-diisopropyl-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate 作用下， 以 氘代苯 为溶剂， 反应 4.0h， 以94%的产率得到3-methyl-1-tosylpyrrolidine
  参考文献：
  名称：

  N-杂环碳烯·硼烷可自由基还原卤代物时，二硫化物和硼烷基硫化物既是引发剂又是前催化剂

  摘要：

  AbstractDiphenyl disulfide (PhSSPh), a typical boryl monosulfide (diiPr‐Imd‐BH2SPh) and a typical boryl bis‐sulfide [diMe‐Imd‐BH(SPh)2] all serve as both initiators and precatalysts in the reduction of alkyl and aryl halides by readily available 1,3‐dimethylimidazol‐2‐ylidene⋅borane (diMe‐Imd‐BH3). The reactions are suggested to occur by a polarity reverse catalysis mechanism where in situ generated thiophenol is the active catalyst.magnified image

  DOI：

  10.1002/adsc.201300752

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。
• Ring Lithiation and Functionalization of Imidazol-2-ylidene-boranes
  作者：Andrey Solovyev、Emmanuel Lacôte、Dennis P. Curran

  DOI：10.1021/ol202516c

  日期：2011.11.18

  N,N′-Dialkyl and N,N′-diaryl imidazol-2-ylidene-boranes and trifluoroboranes are rapidly lithiated at C4 of the imidazole ring, and the resulting intermediates have been quenched with an assortment of electrophiles to provide ring-functionalized imidazol-2-ylidene-boranes. Further deprotonation and functionalization of C5 have been demonstrated. Deboronation of the products by treatment with triflic

  N，N'-二烷基和N，N'-二芳基咪唑-2-亚甲基-硼烷和三氟硼烷在咪唑环的C4处快速锂化，所得中间体已用各种亲电试剂淬灭以提供环官能化的咪唑-2-亚烷基-硼烷。已经证明了C5的进一步去质子化和功能化。通过用三氟甲磺酸或碘处理，然后用甲醇处理使产物脱硼，为制备C4 / C5官能化的咪唑鎓盐和咪唑-2-亚烷基开辟了一条途径。