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通过C-N键裂解实现镍催化芳基和苄基三甲基铵盐的硼化反应

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

作者信息

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

机构信息

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.

出版信息

J Org Chem. 2016 Jan 4;81(1):14-24. doi: 10.1021/acs.joc.5b02557. Epub 2015 Dec 15.

Abstract

By developing a mild Ni-catalyzed system, a method for direct borylation of sp(2) and sp(3) C-N bonds has been established. The key to this hightly efficient C-N bond borylative cleavage depends on the appropriate choice of the nickel catalyst Ni(COD)2, ICy·HCl as a ligand, and the use of 2-ethoxyethanol as the cosolvent. This transformation 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.

摘要

通过开发一种温和的镍催化体系,建立了一种对sp(2)和sp(3) C-N键进行直接硼化的方法。这种高效的C-N键硼化裂解的关键取决于镍催化剂Ni(COD)2、作为配体的ICy·HCl的恰当选择,以及使用2-乙氧基乙醇作为助溶剂。这种转化表现出良好的官能团兼容性,并且可以作为一种用于克级合成以及复杂化合物后期C-N硼化的强大合成工具。

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