Electrochemical Selective Mono‐ and Polychlorination of Substituted Thiophenes

Abstract

An environmentally friendly and efficient electrochemical chlorination of thiophenes has been developed. The monochlorination, dichlorination, and trichlorination of thiophenes are selectively achieved. Notably, the reaction has the merits of mild conditions, excellent functional group tolerance, high yields and selectivity, and the capacity for scale‐up, thus providing a synthetically useful alternative to access mono‐ and polychlorinated thiophenes.

Electrocatalytic conversion of ω-azido carboxylic acids to 1-pyrrolines via a combined process of oxidative decarboxylation and intramolecular Schmidt rearrangement

“…The reaction of the 2-thiophyl substrate was examined, and pyrroline 2y was produced in 30% yield, and the low conversion efficiency may be due to the fact that thiophene is easily oxidized under electrolysis conditions. 55 A secondary azide was tested, and the desired pyrroline 2z was isolated in 45% yield, suggesting that the Schmidt reaction of an azide with a carbocation is sensitive to the steric hindrance. A scale-up reaction of 1a (2.0 mmol) was also carried out, affording 2a in 70% yield after 220 minutes of electrolysis.…”