Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 39, Pages 11443-11447Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505193
Keywords
heterocycles; photochemisty; radicals; reaction mechanisms; synthetic methods
Categories
Funding
- NSFC [21072044, U1204207]
- Czech Science Foundation [13-01061S]
- [14IRTSTHN006]
- [NCET-11-0938]
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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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