Radical‐Based C−C Bond‐Forming Processes Enabled by the Photoexcitation of 4‐Alkyl‐1, 4‐dihydropyridines. (24th October 2017)

• Record Type: Journal Article
• Authors: Buzzetti, Luca; Prieto, Alexis; Roy, Sudipta Raha; Melchiorre, Paolo
• Is Part Of: Angewandte Chemie. Volume 129:Number 47(2017)
• Page Start: 15235
• Page End: 15239
• Publication Date: 2017-10-24
• Subjects: Dihydropyridine -- Kreuzkupplungen -- Nickel-Katalyse -- Photochemie -- Synthesemethoden; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201709571
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: We report herein that 4‐alkyl‐1, 4‐dihydropyridines (alkyl‐DHPs) can directly reach an electronically excited state upon light absorption and trigger the generation of C(sp 3 )‐centered radicals without the need for an external photocatalyst. Selective excitation with a violet‐light‐emitting diode turns alkyl‐DHPs into strong reducing agents that can activate reagents through single‐electron transfer manifolds while undergoing homolytic cleavage to generate radicals. We used this photochemical dual‐reactivity profile to trigger radical‐based carbon–carbon bond‐forming processes, including nickel‐catalyzed cross‐coupling reactions.