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B(C 6 F 5 ) 3 -catalyzed β-C(sp 3 )-H alkylation of tertiary amines with 2-aryl-3 H -indol-3-ones.

Chang-Peng ZouTao MaXiu-Xiu QiaoXi-Xi WuGanpeng LiYonghui HeXiao-Jing Zhao
Published in: Organic & biomolecular chemistry (2023)
The β-C-H functionalization of amines is one of the most powerful tools for the synthesis of saturated nitrogen-containing heterocycles in organic synthesis. However, the β-C-H functionalization of amines via redox-neutral addition with cyclic-ketimines is still unprecedented. Herein, the β-C-H functionalization of tertiary amines is described, providing the corresponding 1,3-diamines containing the indolin-3-one moiety in high yields via the B(C 6 F 5 ) 3 -catalyzed borrowing hydrogen strategy. According to the experimental results, a possible catalytic cycle has been proposed to rationalize the process of this reaction. Notably, the β-C-H alkylation of amines is external oxidant- and transition-metal-free, which makes a significant contribution to promoting economical chemical synthesis.
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