Stepwise Nucleophilic Substitution to Access Saturated N-heterocyclic Carbene Haloboranes with Boron–Methyl Bonds,Organometallics

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Stepwise Nucleophilic Substitution to Access Saturated N-heterocyclic Carbene Haloboranes with Boron–Methyl Bonds
Organometallics ( IF 2.5 ) Pub Date : 2020-12-14 , DOI: 10.1021/acs.organomet.0c00691
Gargi Kundu _{1,

2} , Sanjukta Pahar _{1,

2} , Srinu Tothadi ₃ , Sakya S. Sen _{1,

2}

Affiliation

Compounds of boranes with N-heterocyclic carbenes are known, yet little attention has been paid to NHC compounds of boron bearing methyl and halogen moieties together. The reason can be attributed to the hazardous methyldichloroborane (MeBCl₂), which ignites in air. We describe here convenient solution-phase access to SIDipp·MeBCl₂ (SIDipp = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene) (3) by a salt metathesis reaction of SIDipp·BCl₃ (2) with MeLi. Replacement of the chlorine atoms of 3 with stepwise addition of AgOTf led to the formation of SIDipp·MeBCl(OTf) (4) and SIDipp·MeB(OTf)₂ (5). In the case of 4, all of the substituents on the boron atom are different. Subsequently, we extended our synthetic approach to the amidinate system and prepared PhC(NtBu)₂B(Me)Cl (7) from the reaction of PhC(NtBu)₂BCl₂ (6) with MeLi.

中文翻译：

逐步的亲核取代作用，以饱和的具有硼-甲基键的N-杂环碳卤杂环烷

硼烷与N-杂环卡宾的化合物是已知的，但是很少关注一起带有甲基和卤素部分的硼的NHC化合物。原因可以归因于在空气中点燃的有害甲基二氯硼烷（MeBCl ₂）。我们在这里描述了通过SIDipp·BCl ₃（2）的盐复分解反应方便地溶液相访问SIDipp·MeBCl ₂（SIDipp = 1,3-双（2,6-二异丙基苯基）咪唑啉-2-亚烷基）（3）与MeLi。的氯原子的置换3与分步加入的AgOTf导致形成SIDipp·MeBCl（OTF）（的4）和SIDipp·MEB（OTF）₂（5）。在4的情况下，硼原子上的所有取代基均不同。随后，我们将合成方法扩展到the酰胺体系，并通过PhC（N t Bu）₂ BCl ₂（6）与MeLi的反应制备了PhC（N t Bu）₂ B（Me）Cl（7）。

更新日期：2020-12-28

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