1,2-Migration Enabled Borylation of Benzylic Quaternary Ammonium

doi:10.6023/cjoc202209039

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1868-1874.DOI: 10.6023/cjoc202209039 Previous Articles Next Articles

Special Issue: 有机硼化学专辑

ARTICLES

1,2-迁移促进的苄基季铵盐硼化反应研究

秦玉承^a^,^b, 徐良轩^a^,^b, 徐佳能^a^,^b, 刘超^a^,^*()

a 中国科学院兰州化学物理研究所羰基合成与选择性氧化国家重点实验室兰州 730000
b 中国科学院大学北京 100049

收稿日期:2022-09-30 修回日期:2022-11-16 发布日期:2022-12-21
通讯作者: 刘超
基金资助:
国家自然科学基金(22022113)

1,2-Migration Enabled Borylation of Benzylic Quaternary Ammonium

Yucheng Qin^a^,^b, Liangxuan Xu^a^,^b, Jianeng Xu^a^,^b, Chao Liu^a()

a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
b University of Chinese Academy of Sciences, Beijing 100049

Received:2022-09-30 Revised:2022-11-16 Published:2022-12-21
Contact: Chao Liu
Supported by:
National Natural Science Foundation of China(22022113)

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Abstract

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.

Key words: benzylic quaternary ammonium, borylation, benzylboronic esters, 1,2-migration

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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.

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References 30

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1,2-迁移促进的苄基季铵盐硼化反应研究

1,2-Migration Enabled Borylation of Benzylic Quaternary Ammonium

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