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J Org Chem ; 87(24): 16449-16457, 2022 12 16.
Article in English | MEDLINE | ID: mdl-36455265

ABSTRACT

The replacement of fossil resources with biomass resources in the construction of N-heterocycles is rapidly attracting research interest. Herein, we report palladium-catalyzed selective hydrogenative coupling of nitroarenes and phenols based on a transfer hydrogenation strategy, allowing straightforward access to spirocyclic pyrrolo- and indolo-fused quinoxalines, a class of compounds found in numerous natural alkaloids. The synthetic protocol is characterized by a broad substrate scope and the utilization of biomass-derived reactants and commercially available catalysts. In such transformations, high-pressure and explosive hydrogen are not required. This report provides a new protocol for converting biomass-derived phenols into value-added nitrogen-containing chemicals.


Subject(s)
Palladium , Quinoxalines , Palladium/chemistry , Quinoxalines/chemistry , Phenols , Catalysis , Hydrogenation
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