6533b829fe1ef96bd12896ef
RESEARCH PRODUCT
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subject
010405 organic chemistryPeptidomimetic010402 general chemistryElectrosynthesis01 natural sciencesCombinatorial chemistryCatalysis0104 chemical sciencesProtein–protein interactionCatalysischemistry.chemical_compoundchemistryPyridinePhenolsPhysical and Theoretical ChemistryTrifluoromethanesulfonateAlpha helixdescription
Teraryl-based alpha-helix mimetics have resulted in efficient inhibitors of protein-protein interactions (PPIs). Extending the concept to even longer oligoarene systems would allow for the mimicking of even larger interaction sites. We present a highly efficient synthetic modular access to quateraryl alpha-helix mimetics, in which, at first, two phenols undergo electrooxidative dehydrogenative cross-coupling. The resulting 4,4′-biphenol is then activated by conversion to nonaflates, which serve as leaving groups for iterative Pd-catalyzed Suzuki-cross-coupling reactions with suitably substituted pyridine boronic acids. This work, for the first time, demonstrates the synthetic efficiency of using both electroorganic as well as transition-metal catalyzed cross-coupling in the assembly of oligoarene structures.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-03-19 | Catalysts |