Copper/Silver Cocatalyzed Regioselective C5–H Functionalization of 8-Aminoquinoline Amides with 1,3-Dicarbonyl Compounds

Fuxu Zhan; Wei Zhang; Huaiqing Zhao

doi:10.1055/s-0039-1690806

Synthesis, Table of Contents

Synthesis 2020; 52(07): 1007-1014
DOI: 10.1055/s-0039-1690806

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Copper/Silver Cocatalyzed Regioselective C5–H Functionalization of 8-Aminoquinoline Amides with 1,3-Dicarbonyl Compounds

Authors

Fuxu Zhan

^aSchool of Chemistry and Chemical Engineering, University of Jinan, Jinan, Shandong, 250022, P. R. of China
Wei Zhang

^aSchool of Chemistry and Chemical Engineering, University of Jinan, Jinan, Shandong, 250022, P. R. of China
Huaiqing Zhao∗

^aSchool of Chemistry and Chemical Engineering, University of Jinan, Jinan, Shandong, 250022, P. R. of China

^bState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. of China Email: chm_zhaohq@ujn.edu.cn

Abstract

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Abstract

A copper/silver co-catalyzed cross-dehydrogenative coupling reaction is developed to achieve exclusively remote C5–H coupling of 8-aminoquinoline amides with the methylenic sp³ C–H bond of 1,3-dicarbonyl compounds. This protocol provides a highly regioselective synthetic route for the functionalization of 8-aminoquinoline amides at C5 under mild conditions. Preliminary experiments reveal that radicals may be involved in this catalytic transformation.

Key words

copper - silver - 8-aminoquinoline amides - 1,3-dicarbonyl compounds - C5–H functionalization

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References

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Supplementary Material

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