Photoredox-enabled remote radical group migration: Pathway to 1,7-dicarbonyl compounds from diazoalkanes

Abstract

Herein, we developed a mild and efficient photoredox-enabled remote radical group migration with the utilization of diazoalkanes as radical precursors, giving access to various valuable 1,7-dicarbonlys in moderate to good yields. A diverse set of migrating groups, including benzothiazole, benzothiophene, pyrazine, pyridine, thiazole, thiophene and nitrile were well tolerated. Furthermore, the facile synthesis of 1,8-dicarbonyl compound, scale-up reaction and useful synthetic transformation further proved the method attractive and valuable.

Keywords

• 1,n-dicarbonyls
• Radical migration
• Diazoalkanes
• Visible light
• Photoredox catalysis