Journal
HELVETICA CHIMICA ACTA
Volume 103, Issue 12, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.202000184
Keywords
aerobic oxidation; aza-Henry reaction; cross-coupling; cross-dehydrogenative coupling; phenazines; polymers; porous organic polymers
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Funding
- Projekt DEAL
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The redox activity of molecular phenazine catalysts has been previously exploited for aerobic oxidative amine homo- and cross-coupling reactions. In this contribution, we have extended the reaction scope of this novel type of organocatalyst and used them in the cross-dehydrogenative aza-Henry coupling of isoquinolines with nitromethane under aerobic conditions. Additionally, we have designed and prepared a novel porous organic polymer by cross-linking of tetrakis(4-bromophenyl)silane and dihydrophenazine through Pd-catalyzed Buchwald-Hartwig cross-coupling. This new type of heterogeneous catalyst, apart from being robust and easily reusable, also showed outstanding catalytic activities and improved selectivity compared to its molecular counterpart. A plausible reaction mechanism was proposed based on spectroscopic and kinetic measurements.
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