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.
Keywords: cross-coupling; dihydropyridines; nickel catalysis; photochemistry; synthetic methods.
© 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.