The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16410 - 16423

Опубликована: Ноя. 9, 2023

Three-component alkene 1,2-difunctionalizations have emerged as a powerful strategy for rapid buildup of diverse and complex alkylpyridines, but the distal functionalized alkyl radicals 1,2-alkylpyridylations were still rare. Herein, we report an example regioselective three-component 1,2-cyanoalkylpyridylation feedstock styrenes with accessible nonredox-active cyclic oximes through visible-light photoredox catalysis, providing series structurally β-cyanoalkylated alkylpyridines. This protocol proceeds radical relay pathway including generation iminyl enabled by phosphoranyl radical-mediated β-scission, transposition C-C bond cleavage, highly selective addition, precise radical-radical cross-coupling sequence, thus facilitating formation two distinct single bonds in single-pot operation. synthetic features mild conditions, broad compatibility functional groups substrate scope, product derivatization, late-stage modification.

Язык: Английский