Base-Mediated Borylsilylation/Silylation of Ammonium Salts with Silylborane

Wan-Ying Qi, Jing-Song Zhen, Xiao-hong Xu, Xian Du, Yi-hui Li, Han Yuan, Yun-Shi Guan, Xun Wei, Zi-Ying Wang, Guohai Liang* and Yong Luo*

*South China Normal University, Guangzhou 510631; Sun Yat-sen University, Guangzhou 510275, China, Email: liangguohscnu.edu.cn, luoyong5mail.sysu.edu.cn

W.-Y. Qi, J.-S. Zhen, X.-h. Xu, X. Du, Y.-h. Li, H. Yuan, Y.-S. Guan, X. Wei, Z.-Y. Wang, G. Liang, Y. Luo, Org. Lett., 2021, 23, 5988-5992.

DOI: 10.1021/acs.orglett.1c02066

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Abstract

A base-mediated borylsilylation of benzylic ammonium salts provides geminal silylboronates bearing benzylic proton under mild reaction conditions. Deaminative silylation of aryl ammonium salts was also achieved in the presence of LiOtBu. Both methods offer high efficiency, mild reaction conditions, and good functional group tolerance for late-stage functionalization of amines.

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Key Words

1,1-silylboronates, arylsilanes

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ID: J54-Y2021