Transalkylation via C-N Bond Cleavage of Amines Catalyzed by Super Organophotoreductant CBZ6.

The super organoreductant CBZ6-catalyzed tandem transalkylation-cyclization using amines as traceless radical donors and stabilizer is reported. The later-stage breaking of an N-C bond enables the transalkylation with a secondary amine as the leaving moiety. A wide range of tertiary amines were used as alkyl radical donors for the C1-C8 alkyls. This traceless stabilizer also enabled the transalkylation with methyl radical, which is normally not possible because of the instability of methyl radical.

Ambient Temperature Dehydrogenative C(Ar)-H Carbonylative Lactamization of 2-Arylanilines Using DMF as C1-Source.

The direct dehydrogenative C-H cleaving carbonylative lactamization of 2-arylanilines promoted by visible light and potassium bases is reported. Solvent DMF acts as the sole carbonyl source in the absence of an oxidant. The irreversible release of hydrogen gas drags this reaction to the stable phenanthridinone products. This work provides a direct conversion of a broad range of 2-arylanilines to various phenanthridinones. This method could be applied in the synthesis of bioactive molecules and organic optoelectronic materials.