Electrochemical Radical Selenylation/1,2-Carbon Migration and Dowd–Beckwith-Type Ring-Expansion Sequences of Alkenylcyclobutanols

Abstract

Electrochemical oxidative radical selenylation/1,2-carbon migration and Dowd-Beckwith-type ring-expansion sequences of alkenylcyclobutanols were developed in this study. This approach is environmentally benign and uses shelf-stable diselenides as selenium radical precursors and electrons as oxidizing reagents. The present protocol offers a facile way to prepare β-selenated cyclic ketone derivatives. Under Dowd-Beckwith-type rearrangement, it can afford the corresponding one-carbon ring-expanded ketones.