Metal-free reductive cleavage of C-N and S-N bonds by photoactivated electron transfer from a neutral organic donor

O'Sullivan, Steven and Doni, Eswararao and Tuttle, Tell and Murphy, John A (2014) Metal-free reductive cleavage of C-N and S-N bonds by photoactivated electron transfer from a neutral organic donor. Angewandte Chemie International Edition, 53 (2). 474–478. ISSN 1433-7851

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    Abstract

    A photoactivated neutral organic super electron donor cleaves challenging arenesulfonamides derived from dialkylamines at room temperature. It also cleaves a) ArC[BOND]NR and b) ArN[BOND]C bonds. This study also highlights the assistance given to these cleavage reactions by the groups attached to N in (a) and to C in (b), by lowering LUMO energies and by stabilizing the products of fragmentation.