Combining photoredox catalysis and hydrogen atom transfer for dearomative functionalization of electron rich heteroarenes.

ABSTRACT: Reductive dearomatization has been a broadly explored means for rapid generation of sp³ complexity from simple planar arenes. Breaking the electron rich, stable aromatic systems requires strong reduction conditions. It has been notoriously challenging to dearomatize electron even richer heteroarenes. Herein we report an umpolung strategy enabling dearomatization of such structures under mild conditions. The reversal of the reactivity of these electron rich aromatics via photoredox mediated single electron transfer (SET) oxidation generates electrophilic radical cations, which can react with nucleophiles and break the aromatic structure to form a Birch type radical species. A crucial hydrogen atom transfer (HAT) is successfully engineered into the process to efficiently tr

SUBMITTER: Ji P 

PROVIDER: S-EPMC10034082 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature