0000000000019919

AUTHOR

Benedikt Dahms

showing 6 related works from this author

Synthesis of Optically Pure Arylamine Derivatives by Using the Bucherer Reaction

2017

The Bucherer reaction is a common pathway for the conversion of 1- and 2-naphthols into the corresponding 1- or 2-naphthylamines, respectively. Mostly, only singular examples for its preparative use are reported since this particular transformation seems to be very sensitive to the reaction conditions. By choosing different phenolic substrates and chiral amines, we were able to prepare a broad scope of optically pure arylamines using this type of reaction. In contrast to alternative methods forming C−N aryl bonds such as Buchwald-Hartwig or Chan-Lam cross-coupling reactions, no palladium or copper catalysts are required. The use of water as solvent and the easily available starting material…

Reaction conditionsAlternative methodsBucherer reaction010405 organic chemistryArylchemistry.chemical_elementGeneral Chemistry010402 general chemistry01 natural sciencesCopper0104 chemical sciencesCatalysisSolventchemistry.chemical_compoundchemistryOrganic chemistryPalladiumChemistrySelect
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Selective Formation of 4,4'-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction.

2019

A simple and selective electrochemical synthesis by dehydrogenative coupling of unprotected 2,6- or 2,5-substituted phenols to the desired 4,4'-biphenols is reported. Using electricity as the oxidizing reagent avoids pre-functionalization of the starting materials, since a selective activation of the substrates takes place. Without the necessity for metal-catalysts or the use of stoichiometric reagents it is an economic and environmentally friendly transformation. The elaborated electrochemical protocol leads to a broad variety of the desired 4,4'-biphenols in a very simplified manner compared to classical approaches. This is particular the case for the cross-coupled products.

010405 organic chemistryChemistryOrganic ChemistryGeneral Chemistry010402 general chemistryElectrochemistry01 natural sciencesEnvironmentally friendlyCombinatorial chemistryCatalysisCoupling reaction0104 chemical sciencesAnodeReagentOxidizing agentDehydrogenationStoichiometryChemistry (Weinheim an der Bergstrasse, Germany)
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Metal‐ and Reagent‐Free Anodic Dehydrogenative Cross‐Coupling of Naphthylamines with Phenols

2018

Materials science010405 organic chemistryInorganic chemistry010402 general chemistryElectrochemistry01 natural sciencesCatalysis0104 chemical sciencesAnodeMetalCoupling (electronics)chemistry.chemical_compoundchemistryReagentvisual_artElectrochemistryvisual_art.visual_art_mediumDehydrogenationPhenolsChemElectroChem
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Front Cover: Metal‐ and Reagent‐Free Anodic Dehydrogenative Cross‐Coupling of Naphthylamines with Phenols (ChemElectroChem 9/2018)

2018

Materials sciencePhotochemistryElectrochemistryCatalysisAnodeCoupling (electronics)Metalchemistry.chemical_compoundFront coverchemistryReagentvisual_artElectrochemistryvisual_art.visual_art_mediumDehydrogenationPhenolsChemElectroChem
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CCDC 1858697: Experimental Crystal Structure Determination

2019

Related Article: Benedikt Dahms, Philipp J. Kohlpaintner, Anton Wiebe, Rolf Breinbauer, Dieter Schollmeyer, Siegfried R. Waldvogel|2019|Chem.-Eur.J.|25|2713|doi:10.1002/chem.201805737

Space GroupCrystallographyCrystal SystemCrystal Structure35-dimethoxy-3'5'-bis(propan-2-yl)[11'-biphenyl]-44'-diolCell ParametersExperimental 3D Coordinates
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CCDC 1858698: Experimental Crystal Structure Determination

2019

Related Article: Benedikt Dahms, Philipp J. Kohlpaintner, Anton Wiebe, Rolf Breinbauer, Dieter Schollmeyer, Siegfried R. Waldvogel|2019|Chem.-Eur.J.|25|2713|doi:10.1002/chem.201805737

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates3'5'-dimethoxy-25-dimethyl[11'-biphenyl]-44'-diol
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