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Metal-Free C(sp2)-H/N-H Cross-Dehydrogenative Coupling of Quinoxalinones with Aliphatic Amines under Visible-Light Photoredox Catalysis

Wei Wei*, Leilei Wang, Pengli Bao, Yun Shao, Huilan Yue, Daoshan Yang, Xiaobo Yang, Xiaohui Zhao*, Hua Wang

*Qinghai Provincial Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Qinghai 810008, China, Email: weiweiqfnu163.com, xhzhaonwipb.cas.cn

W. Wei, L. Wang, P. Bao, Y. Shao, H. Yue, D. Yang, X. Yang, X. Zhao, H. Wang, Org. Lett., 2018, 20, 7125-7130.

DOI: 10.1021/acs.orglett.8b03079 (free Supporting Information)



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Abstract

An efficient visible-light-induced C(sp2)-H/N-H cross-dehydrogenative coupling (CDC)-amination with both primary and secondary aliphatic amines allows the direct formation of 3-aminoquinoxalin-2(1H)-ones. Preliminary mechanistic studies reveal that the reaction proceeds through a radical process.

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proposed mechanism



Key Words

quinoxalin-2(1H)-ones, oxygen, photochemistry


ID: J54-Y2018