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Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C-N Bond Cleavage

Jiefeng Hu, Heqing Sun, Wangshui Cai, Xinghui Pu, Yemin Zhang and Zhuangzhi Shi*

*State Key Laboratory of Coordination Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China, Email: shiznju.edu.cn

J. Hu, H. Sun, W. Cai, X. Pu, Y. Zhang, Z. Shi, J. Org. Chem., 2016, 81, 14-24.

DOI: 10.1021/acs.joc.5b02557 (free Supporting Information)



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Abstract

The appropriate choice of a nickel catalyst Ni(COD)2, ICy·HCl as a ligand, and the use of 2-ethoxyethanol as the cosolvent enables a highly efficient C-N bond borylative cleavage of sp2 and sp3 C-N bonds. This reaction shows good functional group compatibility and can serve as a powerful synthetic tool for gram-scale synthesis and late-stage C-N borylation of complex compounds.

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Key Words

boronates


ID: J42-Y2016