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

Org Biomol Chem

Key Laboratory of Chemistry in Ethnic Medicinal Resources, Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, State Ethnic Affairs Commission & Ministry of Education, School of Ethnic Medicine, Yunnan Minzu University, Kunming, 650500, China.

Published: May 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 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 the B(CF)-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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http://dx.doi.org/10.1039/d3ob00481cDOI Listing

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