Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 47, Pages 15039-15043Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709571
Keywords
cross-coupling; dihydropyridines; nickel catalysis; photochemistry; synthetic methods
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Funding
- Generalitat de Catalunya (CERCA Program)
- European Research Council [ERC-2015-CoG 681840-CATA-LUX]
- MINECO [CTQ2013-45938-P, CTQ2016-75520-P]
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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.
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