Photo-Driven Regiodivergent\nArylation/Cyclization\nand Arylation/Hydroxylation of <i>N</i>‑Aryl Methacrylamides\nwith Aryltriazenes: Access to Functionalized 3,3-Disubstituted Oxindoles\nand α‑Hydroxylamides

A metal-free, light-induced regiodivergent functionalization\nof\nα,β-unsaturated amides with aryltriazenes under ambient\nconditions was developed. The visible light and B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> cocatalyzed radical cascade arylation/cyclization\nof <i>N</i>-alkyl-<i>N</i>-arylmethacrylamides\ncan obtain functionalized 3,3-disubstituted oxindoles with the assistance\nof photocatalyst eosin Y–Na<sub>2</sub>. In the absence of\nany catalyst, with purple light irradiation and electron-donor–acceptor\n(EDA) complex initiation, the radical cascade arylation/hydroxylation\nof <i>N</i>-arylmethacrylamides affords α-hydroxylamides.\nThis methodology highlights the arts in accessing different regioisomers\nby altering the substrates and photocatalytic strategies.