Light-Driven Organocatalytic Birch Reduction for Late-Stage Drug Modification and sp³-Rich Spirocycle Synthesis.

ABSTRACT: The Birch reduction is a cornerstone transformation in synthetic chemistry, yet its widespread application is limited by harsh conditions, poor functional group tolerance, and safety concerns. Recent photochemical strategies have offered milder alternatives but have largely been restricted to polycyclic arenes (E_red ∼ -2.6 V vs SCE) and poorly suited for complex molecules of pharmaceutical relevance. Here, we report a practical organocatalytic system that enables Birch-type reductions of electron-rich benzenes (E_red = <-3.4 V vs SCE) and heteroarenes under light irradiation and mild conditions. The method is based on an indoline-2-thione anion catalyst developed from our previously reported organic super-reducing photocatalysts. The protocol exhibits a b

SUBMITTER: Schiel F 

PROVIDER: S-EPMC12903859 | biostudies-literature | 2026 Feb

REPOSITORIES: biostudies-literature