期刊
CHEMICAL COMMUNICATIONS
卷 58, 期 44, 页码 6429-6432出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc01404a
关键词
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资金
- Scientific Research Project of Education Department of Hubei Province [B2020057]
- Open Fund of the Jiangxi Province Key Laboratory of Synthetic Chemistry [JXSC202002]
A highly selective alkylation method of indazoles is described in this paper, which does not require a metal catalyst and shows high yields and excellent functional group tolerance.
Selective alkylation of indazoles is still a highly challenging topic in chemistry and the synthesis of important molecules. Herein, a novel highly selective N-2-alkylation of indazoles with diazo compounds is described in the presence of TfOH. Unlike the traditional metal- and base-catalysed version, this protocol highlights the regioselectivity of alkylation of indazoles and a metal-free catalysis system, affording N-2-alkylated products in good to excellent yields with high regioselectivity (N-2/N-1 up to 100/0) and excellent functional group tolerance. Furthermore, a gram scale synthesis was conducted successfully to give rise to the corresponding products. Mechanistic studies through control experiments provide plausible mechanistic proposals.
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