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六元氮杂环卡宾·硼烷在硼原子处的取代反应:便捷合成二羟基硼鎓阳离子

Substitution at sp boron of a six-membered NHC·BH: convenient access to a dihydroxyborenium cation.

作者信息

Kundu Gargi, Ajithkumar V S, Raj K Vipin, Vanka Kumar, Tothadi Srinu, Sen Sakya S

机构信息

Inorganic Chemistry and Catalysis Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411008, India.

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India.

出版信息

Chem Commun (Camb). 2022 Mar 18;58(23):3783-3786. doi: 10.1039/d1cc06816d.

DOI:10.1039/d1cc06816d
PMID:35229841
Abstract

Herein, we have undertaken the synthesis and investigated the reactivity of a 6-membered saturated NHC borane adduct (1). Direct electrophilic halogenation of 1 with a stoichiometric amount of I led to NHC boryl iodides, 6-SIDipp·BHI (2) and 6-SIDipp·BHI (3), which were further reacted with various nucleophiles to give novel 6-SIDipp based mono and disubstituted boranes with OTf (4 and 6) or ONO (5 and 7) functional groups. The addition of Br/HO to 1 smoothly results in a dihydroxyborenium cation (8).

摘要

在此,我们进行了六元饱和NHC硼烷加合物(1)的合成,并研究了其反应活性。用化学计量的碘对1进行直接亲电卤化反应,得到了NHC硼基碘化物6-SIDipp·BHI(2)和6-SIDipp·BHI(3),它们进一步与各种亲核试剂反应,得到了具有OTf(4和6)或ONO(5和7)官能团的新型基于6-SIDipp的单取代和双取代硼烷。将Br/HO添加到1中可顺利生成二羟基硼鎓阳离子(8)。

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