(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)*BH₂I | 1207374-64-8

• 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)*BH₂I
• 英文别名: IPr*BH₂I；IDipp·BH₂I；1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene iodoborane；1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene boryl iodide；[1,3-Bis[2,6-di(propan-2-yl)phenyl]imidazol-1-ium-2-yl]-iodoboranuide
• CAS: 1207374-64-8
• 化学式: C₂₇H₃₈BIN₂
• 分子量: 528.328
• InChiKey: WESKEPQXFKZHNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)*BH₂I 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成 [(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)*BH₂NH₃]OTf
  参考文献：
  名称：

  N-杂环卡宾配位氨基硼烷配合物的合成、结构和反应性

  摘要：

  由于其独特的特性，最近的研究引起了对 N-杂环卡宾配位硼烷 (NHC-borane) 及其 B-取代衍生物的相当大的关注。在目前的工作中，我们专注于此类胺络合物的合成、结构和反应性，[NHC·BH 2 NH 3 ]X ((NHC = IPr (1,3-bis(2,6-diisopropylphenyl)imidazol -2-ylidene) and IMe (1,3-dimethylimidazol-2-ylidene); X = Cl, I, OTf). 我们开发了一种通过NaH与[IPr反应得到NHC·BH 2 NH 2的合成方法·BH 2 NH 3 ]I，由IPr·BH 2 I与NH 3反应合成。作为路易斯碱，NHC·BH2 NH 2可进一步与HCl或HOTf反应生成相应的盐类[IPr·BH 2 NH 3 ] +。IPr·BH 2 NH 2 BH 2 X (X = Cl, I)由HCl/I

  DOI：

  10.1021/acs.inorgchem.3c00930
• 作为产物：
  描述：

  1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene 以 甲苯 、 苯 为溶剂， 反应 2.0h， 生成 (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)*BH₂I
  参考文献：
  名称：

  NHC·GaH2(OTf) 加合物的一般途径——合成 NHC 稳定的镓阳离子 13/15 链化合物的关键

  摘要：

  报道了NHC 稳定的三氟甲磺酸镓 NHC ⋅ GaH 2 (OTf) (NHC=IDipp, IMes, IPr 2 Me 2 ) 的一般合成途径。这些化合物被用作构建块，以获得前所未有的 13/15 较重族 13 元素的阳离子链化合物 [IDipp ⋅ GaH 2 PR 2 EH 2  ⋅ D] (R=H, Ph; D=NMe 3 , IDipp; E=乙，加）。所有化合物均通过单晶 X 射线结构测定进行表征，并通过计算方法阐明电子特征。

  DOI：

  10.1002/chem.202301752

文献信息

• Generation and Reactions of an Unsubstituted N-Heterocyclic Carbene Boryl Anion
  作者：Julien Monot、Andrey Solovyev、Hélène Bonin-Dubarle、Étienne Derat、Dennis P. Curran、Marc Robert、Louis Fensterbank、Max Malacria、Emmanuel Lacôte

  DOI：10.1002/anie.201004215

  日期：2010.11.22

  unsubstituted N‐heterocyclic carbene (NHC) boryl anion can be generated by reduction, and trapped by electrophiles (see scheme; dipp=2,6‐diisopropylphenyl) to provide new substituted NHC boranes. It is yet another example of a low‐valent boron compound or boron‐containing reactive intermediate stabilized by an NHC, thereby extending the scope of NHC borane chemistry.

  低位：还原可生成锂化的未取代的N-杂环卡宾（NHC）硼基阴离子，并被亲电试剂捕获（请参阅方案; dipp = 2,6-二异丙基苯基）以提供新的取代的NHC硼烷。这是由NHC稳定的低价硼化合物或含硼反应性中间体的又一个例子，从而扩展了NHC硼烷化学的范围。
• Encapsulating Inorganic Acetylene, HBNH, Using Flanking Coordinative Interactions
  作者：Anindya K. Swarnakar、Christian Hering-Junghans、Koichi Nagata、Michael J. Ferguson、Robert McDonald、Norihiro Tokitoh、Eric Rivard

  DOI：10.1002/anie.201504867

  日期：2015.9.1

  coordination complex of the elusive parent inorganic iminoborane HBNH (a structural analogue of acetylene) is reported. This species was generated via thermally induced N2 elimination/1,2‐H migration from a hydrido(azido)borane adduct NHC⋅BH2N3 (NHC=N‐heterocyclic carbene) in the presence of a fluorinated triarylborane. The mechanism of this process was also investigated by computational and isotopic

  据报道，一种不稳定的母体无机亚氨基硼烷HBNH（乙炔的结构类似物）具有稳定的供体-受体配位络合物。该物质是在氟化三芳基硼烷存在下，由氢化（叠氮基）硼烷加合物NHC· BH 2 N 3（NHC = N-杂环卡宾）通过热诱导的N 2消除/ 1,2-H迁移生成的。还通过计算和同位素标记研究研究了该过程的机理。这种转变代表了通往不饱和无机结构单元以进行高级材料合成的新的且可能是模块化的途径。
• Characterization of the Ligand Properties of Donor‐stabilized Pnictogenyltrielanes
  作者：Robert Szlosek、Amelie Sophie Niefanger、Gábor Balázs、Michael Seidl、Alexey Y. Timoshkin、Manfred Scheer

  DOI：10.1002/chem.202303603

  日期：2024.2.26

  The syntheses and characterizations of alkyl-substituted compounds IDipp ⋅ BH2ER2 (E=P, As; R=alkyl) are presented. Together with other donor-stabilized pnictogenyltrielanes, these compounds were reacted with Ni(CO)4 and their ligand properties evaluated regarding the steric and electronic nature of this class of compounds. According to the corresponding Tolman Electronic Parameters, the compounds

  介绍了烷基取代化合物 IDipp ⋅ BH 2 ER 2 (E=P, As;R=烷基) 的合成和表征。这些化合物与其他供体稳定的硝基三烷一起与 Ni(CO) 4反应，并根据此类化合物的空间和电子性质评估其配体性质。根据相应的托尔曼电子参数，这些化合物比常规膦更富电子，并且可以轻松修改其空间和电子需求。
• Substitution Reactions at Tetracoordinate Boron: Synthesis of N-Heterocyclic Carbene Boranes with Boron−Heteroatom Bonds
  作者：Andrey Solovyev、Qianli Chu、Steven J. Geib、Louis Fensterbank、Max Malacria、Emmanuel Lacôte、Dennis P. Curran

  DOI：10.1021/ja107025y

  日期：2010.10.27

  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.).