Visible-Light-Mediated Synthesis of Rutaecarpine Alkaloids through C–N Cross-Coupling Reaction

Author:

Wang Guixia1,Kong Xiangfei1,Chen Dong1,Li Shiqing1,Wang Jinhua2,Gou Tiantian1,Zhang Linfeng1

Affiliation:

1. College of Chemistry and Bioengineering, Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Guilin University of Technology

2. State Key laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University

Abstract

AbstractA visible-light-initiated cross-dehydrogenative-coupling amination is described, featuring metal- and photocatalyst-free, at room temperature, and using air as an oxidant. The reaction provides a facile approach for the synthesis of rutaecarpine and its derivatives. The substrates with electron-withdrawing groups give higher yields than those with electron-donating groups, but the substituent position has a negligible influence on the yield. Using binaphthyl-diyl hydrogen phosphate and dibenzyl phosphate as catalysts both deliver satisfying yields. This straightforward light-driven strategy might be applicable to the synthesis of quinazolinone derivatives.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Guangxi Province

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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