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

Herein we report the conversion of 4-aryl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.

Automated summary

In this study, the conversion of 4-aryl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions is reported. The reaction proceeds via the homolysis of acyl-DHP under electron activation and resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This methodology shows wider functionality tolerance and synthetic utility for late-stage modification of complex molecules.