Visible light-driven dearomative meta-cycloadditions of 2-acetonaphthalenes via triplet energy transfer cascade.

ABSTRACT: Dearomative cycloadditions (DACs) with ortho- and para-variants have been well documented under visible light-mediated triplet-triplet energy transfer (^VLEnT) catalysis. The prospective [3 + 2] or the meta-DACs propelled via ^VLEnT catalysis remains elusive. Classically, meta-DACs are known under harsher UV irradiations and are symmetry allowed in the excited singlet potential energy surface. Herein, we report formal meta-DACs of 2-acetonaphthalenes propagated via a two-step ^VLEnT cascade circumventing the attainment of energetically higher singlet excited states. The photosensitizer selectively promotes the [4 + 2] cycloaddition followed by a contra-thermodynamic di-π-methane type skeleton rearrangement cascade. The DFT studies in conjugation with electroch

SUBMITTER: Rai P 

PROVIDER: S-EPMC11950210 | biostudies-literature | 2025 Mar

REPOSITORIES: biostudies-literature