Redox-neutral photocatalytic hydrodealkenylation of aryl olefins.

ABSTRACT: Carbon-carbon bond cleavage is a transformative strategy in chemical synthesis, particularly for modifying complex molecules. While the cleavage of C(sp²)=C(sp²) π-bonds is relatively straightforward, the selective cleavage of unpolarized C(sp²)-C(sp³) σ-bonds remains a significant challenge. In this study, we present a redox-neutral approach for hydrodealkenylation, enabling the selective cleavage of C(sp²)-C(sp³) σ-bonds in aryl olefins. This reaction proceeds via a cascade of aryl radical cation-mediated open-shell steps under photoredox conditions, incorporating an alkene migration step that exhibits high selectivity and synthetic versatility. This protocol facilitates the selective removal of a vinyl group from arylalkene substrates, yielding isolable fragments. Moreover, this method

SUBMITTER: Liao K 

PROVIDER: S-EPMC12216682 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature