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CuBr-Catalyzed Aerobic Decarboxylative Cycloaddition for the Synthesis of Indolizines under Solvent-Free Conditions

Wenhui Wang, Junwen Han, Jinwei Sun* and Yun Liu*

*Jiangsu Key Laboratory of Green Synthesis for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, Jiangsu P. R. China, Email: gysunjinwei126.com, liu__yun3sina.com

W. Wang, J. Han, J. Sun, Y. Liu, J. Org. Chem., 2017, 82, 2835-2842.

DOI: 10.1021/acs.joc.6b02455 (free Supporting Information)



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Abstract

An efficient synthesis of diversified indolizine derivatives in good yields from pyridines, methyl ketones and alkenoic acids under solvent-free conditions involves a copper-catalyzed bromination of the methyl ketone, 1,3-dipolar cycloaddition of the pyridinium ylide with the alkenoic acid, followed by oxidative decarboxylation and dehydrogenative aromatization of the primary cycloadduct in oxygen atmosphere.


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proposed mechanism



Key Words

indolizines, oxygen, multicomponent reactions


ID: J42-Y2017