Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp³)-H functionalization.

ABSTRACT: A chemodivergent photocatalytic approach to 1-pyrrolines and 1-tetralones from alkyl bromides and vinyl azides has been developed through chemoselectively controllable intermolecular [3 + 2] and [4 + 2] cyclization. This photoredox-neutral two-component protocol involves intermolecular radical addition and switchable distal C(sp³)-H functionalization enabled by iminyl radical-mediated 1,5-hydrogen atom transfer. Meanwhile, chemoselectivity between C(sp³)-N bond formation and C(sp³)-C(sp²) bond formation is precisely switched by photocatalysts (Ru(bpy)₃(PF₆)₂ vs. fac-Ir(ppy)₃) and additives (base vs. acid).

SUBMITTER: Tu S 

PROVIDER: S-EPMC9641198 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature