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Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines

Xiaosheng Luo and Ping Wang*

*School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, China, Email: wangp1sjtu.edu.cn

X. Luo, P. Wang, Org. Lett., 2021, 23, 4960-4965.

DOI: 10.1021/acs.orglett.1c01243 (free Supporting Information)



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Abstract

4-Acyl-1,4-dihydropyridines (DHPs) can be converted into ynones under mild, electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals are alkynylated with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. The reaction tolerates halides, carboxylates, or alkenes.


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proposed reaction pathway



Key Words

alkynylation, electrochemistry


ID: J54-Y2021