Transition Metal Free Intermolecular Direct Oxidative C-N Bond Formation to Polysubstituted Pyrimidines Using Molecular Oxygen as the Sole Oxidant

Wei Guo, Chunsheng Li, Jianhua Liao, Fanghua Ji, Dongqing Liu, Wanqing Wu* and Huanfeng Jiang*

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China, Email: jianghfscut.edu.cn, cewuwqscut.edu.cn

W. Guo, C. Li, J. Liao, F. Ji, D. Liu, W. Wu, H. Jiang, J. Org. Chem., 2016, 81, 5538-5546.

DOI: 10.1021/acs.joc.6b00867

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Abstract

A base-promoted intermolecular oxidation C-N bond formation of allylic C(sp³)-H and vinylic C(sp²)-H of allyllic compounds with amidines enables the smooth formation of polysubstituted pyrimidines in the presence of O₂ as the sole oxidant. This protocol features protecting group free nitrogen sources, good functional group tolerance, high atom economy, and environmental advantages.

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Key Words

pyrimidines, oxygen

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ID: J42-Y2016