Organic Chemistry Portal



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:

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

DOI: 10.1021/acs.orglett.1c01243

see article for more reactions


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.

see article for more examples

proposed reaction pathway

Key Words

alkynylation, electrochemistry

ID: J54-Y2021