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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 (free Supporting Information)


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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


ID: J42-Y2016