3 years ago

Radical-Based C−C Bond-Forming Processes Enabled by the Photoexcitation of 4-Alkyl-1,4-dihydropyridines

Radical-Based C−C Bond-Forming Processes Enabled by the Photoexcitation of 4-Alkyl-1,4-dihydropyridines
Alexis Prieto, Sudipta Raha Roy, Luca Buzzetti, Paolo Melchiorre
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(sp3)-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. Powered by Light: 4-alkyl-1,4-dihydropyridines 1 are primarily understood as hydride sources in their ground state. Excitation with a violet-light-emitting diode transforms them into strong reducing agents that can activate reagents through single-electron transfer while undergoing homolytic cleavage to generate alkyl radicals. This process was used to trigger radical-based C−C bond-forming processes, including nickel-catalyzed cross-coupling reactions.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709571

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