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Controllable Chemoselectivity in Visible-Light Photoredox Catalysis: Four Diverse Aerobic Radical Cascade Reactions.

Angewandte Chemie (International ed. in English) (2015-07-28)
Xinfei Liu, Xinyi Ye, Filip Bureš, Hongjun Liu, Zhiyong Jiang
RÉSUMÉ

Reported is the controllable selectivity syntheses of four distinct products from the same starting materials by visible-light photoredox catalysis. By employing a dicyanopyrazine-derived chromophore (DPZ) as photoredox catalyst, an aerobic radical mechanism has been developed, and allows the reactions of N-tetrahydroisoquinolines (THIQs) with N-itaconimides to through four different pathways, including addition-cyclization, addition-elimination, addition-coupling, and addition-protonation, with satisfactory chemoselectivity. The current strategy provide straightforward access to four different but valuable N-heterocyclic adducts in moderate to excellent yields.

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DPZ, 95%