Chinese Journal of Organic Chemistry >
1,2-Migration Enabled Borylation of Benzylic Quaternary Ammonium
Received date: 2022-09-30
Revised date: 2022-11-16
Online published: 2022-12-21
Supported by
National Natural Science Foundation of China(22022113)
A transition metal-free borylation of quaternary ammonium salts has been reported via a 1,2-boronate migrations using benzyl quaternary ammonium salts as substrates and base (potassium bis(trimethylsilyl)amide, KHMDS) with steric hinderance as hydrogen abstractor, B2pin2 as the boron source. In this transformation, benzylic monoboronate esters and benzylic 1,1-diboronate esters can be obtained by different quenching methods. This transformation showed a favorable tolerance for benzylic quaternary ammonium with different functional groups. A gram scale synthesis was performed.
Yucheng Qin , Liangxuan Xu , Jianeng Xu , Chao Liu . 1,2-Migration Enabled Borylation of Benzylic Quaternary Ammonium[J]. Chinese Journal of Organic Chemistry, 2023 , 43(5) : 1868 -1874 . DOI: 10.6023/cjoc202209039
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