0000000000230658
AUTHOR
Katrin Marie Dyballa
showing 32 related works from this author
Selektive Synthese teilgeschützter unsymmetrischer Biphenole durch reagens‐ und metallfreie anodische Kreuzkupplung
2016
Scalable and Selective Preparation of 3,3′,5,5′-Tetramethyl-2,2′-biphenol
2016
Biphenols are indispensable building blocks in ligand systems for organic catalysis. 3,3′5,5′-Tetramethyl-2,2′-biphenol is a particular versatile motif in different catalytic systems. We developed an easy to perform and scalable process to give access to large quantities of this important building block by the use of selenium dioxide, a common and readily available oxidizer.
Metal- and reagent-free highly selective anodic cross-coupling reaction of phenols.
2014
The direct oxidative cross-coupling of phenols is a very challenging transformation, as homo-coupling is usually strongly preferred. Electrochemical methods circumvent the use of oxidizing reagents or metal catalysts and are therefore highly attractive. Employing electrolytes with a high capacity for hydrogen bonding, such as methanol with formic acid or 1,1,1,3,3,3-hexafluoro-2-propanol, a direct electrolysis in an undivided cell provides mixed 2,2′-biphenols with high selectivity. This mild method tolerates a variety of moieties, for example, tert-butyl groups, which are not compatible with other strong electrophilic media but vital for later catalytic applications of the formed products.
Selective Synthesis of Partially Protected Nonsymmetric Biphenols by Reagent‐ and Metal‐Free Anodic Cross‐Coupling Reaction
2016
The oxidative cross-coupling of aromatic substrates without the necessity of leaving groups or catalysts is described. The selective formation of partially protected nonsymmetric 2,2'-biphenols via electroorganic synthesis was accomplished with a high yield of isolated product. Since electric current is employed as the terminal oxidant, the reaction is reagent-free; no reagent waste is generated as only electrons are involved. The reaction is conducted in an undivided cell, and is suitable for scale-up and inherently safe. The implementation of O-silyl-protected phenols in this transformation results in both significantly enhanced yields and higher selectivity for the desired nonsymmetric 2…
Innentitelbild: Reagens- und metallfreie anodische C-C-Kreuzkupplung von Anilinderivaten (Angew. Chem. 17/2017)
2017
ChemInform Abstract: Solvent-Dependent Facile Synthesis of Diaryl Selenides and Biphenols Employing Selenium Dioxide.
2016
The reaction of phenols (I) with selenium dioxide in pyridine leads to diaryl selenides (IIa-d), whilst the reaction in acetic acid gives rise to biphenols (III).
Cover Picture: Source of Selectivity in Oxidative Cross-Coupling of Aryls by Solvent Effect of 1,1,1,3,3,3-Hexafluoropropan-2-ol (Chem. Eur. J. 35/20…
2015
ChemInform Abstract: Synthesis of meta-Terphenyl-2,2′′-diols by Anodic C-C Cross-Coupling Reactions.
2016
The anodic C−C cross-coupling reaction is a versatile synthetic approach to symmetric and non-symmetric biphenols and arylated phenols. We herein present a metal-free electrosynthetic method that provides access to symmetric and non-symmetric meta-terphenyl-2,2′′-diols in good yields and high selectivity. Symmetric derivatives can be obtained by direct electrolysis in an undivided cell. The synthesis of non-symmetric meta-terphenyl-2,2′′-diols required two electrochemical steps. The reactions are easy to conduct and scalable. The method also features a broad substrate scope, and a large variety of functional groups are tolerated. The target molecules may serve as [OCO]3− pincer ligands.
Source of Selectivity in Oxidative Cross-Coupling of Aryls by Solvent Effect of 1,1,1,3,3,3-Hexafluoropropan-2-ol
2015
Abstract Solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) with a high capacity for donating hydrogen bonds generate solvates that enter into selective cross-coupling reactions of aryls upon oxidation. When electric current is employed for oxidation, reagent effects can be excluded and a decoupling of nucleophilicity from oxidation potential can be achieved. The addition of water or methanol to the electrolyte allows a shift of oxidation potentials in a specific range, creating suitable systems for selective anodic cross-coupling reactions. The shift in the redox potentials depends on the substitution pattern of the substrate employed. The concept has been expanded from arene-phenol…
ChemInform Abstract: Source of Selectivity in Oxidative Cross-Coupling of Aryls by Solvent Effect of 1,1,1,3,3,3-Hexafluoropropan-2-ol.
2016
Abstract Solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) with a high capacity for donating hydrogen bonds generate solvates that enter into selective cross-coupling reactions of aryls upon oxidation. When electric current is employed for oxidation, reagent effects can be excluded and a decoupling of nucleophilicity from oxidation potential can be achieved. The addition of water or methanol to the electrolyte allows a shift of oxidation potentials in a specific range, creating suitable systems for selective anodic cross-coupling reactions. The shift in the redox potentials depends on the substitution pattern of the substrate employed. The concept has been expanded from arene-phenol…
Synthesis ofmeta-Terphenyl-2,2′′-diols by Anodic C−C Cross-Coupling Reactions
2016
The anodic C-C cross-coupling reaction is a versatile synthetic approach to symmetric and non-symmetric biphenols and arylated phenols. We herein present a metal-free electrosynthetic method that provides access to symmetric and non-symmetric meta-terphenyl-2,2''-diols in good yields and high selectivity. Symmetric derivatives can be obtained by direct electrolysis in an undivided cell. The synthesis of non-symmetric meta-terphenyl-2,2''-diols required two electrochemical steps. The reactions are easy to conduct and scalable. The method also features a broad substrate scope, and a large variety of functional groups are tolerated. The target molecules may serve as [OCO](3-) pincer ligands.
Inside Cover: Reagent- and Metal-Free Anodic C−C Cross-Coupling of Aniline Derivatives (Angew. Chem. Int. Ed. 17/2017)
2017
Electro-organic Synthesis as a Sustainable Alternative for Dehydrogenative Cross-Coupling of Phenols and Naphthols
2016
The dehydrogenative cross-coupling of phenols and naphthols can be achieved by several oxidative methods. However, the key is the use of fluorinated alcohols such as 1,1,1,3,3,3-hexafluoroisopropanol. The direct application of electricity represents an alternative synthetic approach, which is superior to other oxidizers (e.g., peroxides). The method is sustainable, inherently safe, and easily scalable.
Synthese vonmeta-Terphenyl-2,2′′-diolen durch anodische C-C-Kreuzkupplungen
2016
Die anodische C-C-Kreuzkupplung ist eine vielseitig einsetzbare Transformation, die eine gezielte Synthese von Biphenolen und arylierten Phenolen ermoglicht. Wir berichten uber einen ebenfalls elektrosynthetischen, metallfreien Ansatz, der einen Zugang zu symmetrischen und nichtsymmetrischen meta-Terphenyl-2,2′′-diolen in guten Ausbeuten und hoher Selektivitat ermoglicht. Symmetrische Derivate konnen durch eine direkte Synthese in einer ungeteilten Zelle gewonnen werden, wohingegen nichtsymmetrische meta-Terphenyl-2,2′′-diole zwei elektrochemische Stufen benotigen. Die milde Methode ist einfach durchzufuhren und skalierbar. Auserdem konnte erstmalig eine breite Substratvariabilitat aufgezei…
Metall- und reagensfreie hochselektive anodische Kreuzkupplung von Phenolen
2014
Cover Picture: Metal‐ and Reagent‐Free Highly Selective Anodic Cross‐Coupling Reaction of Phenols (Angew. Chem. Int. Ed. 20/2014)
2014
Cover Picture: Selective Synthesis of Partially Protected Nonsymmetric Biphenols by Reagent‐ and Metal‐Free Anodic Cross‐Coupling Reaction (Angew. Ch…
2016
Titelbild: Selektive Synthese teilgeschützter unsymmetrischer Biphenole durch reagens‐ und metallfreie anodische Kreuzkupplung (Angew. Chem. 39/2016)
2016
ChemInform Abstract: Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols.
2014
Boron-doped diamond electrodes allow the direct anodic cross-coupling of phenols in hexafluoroisopropanol without using leaving functions or protecting groups.
Reagens- und metallfreie anodische C-C-Kreuzkupplung von Anilinderivaten
2017
Vorgestellt wird die oxidative Kreuzkupplung von Anilinderivaten zu 2,2′-Diaminobiarylen. Der Oxidationsschritt wird elektrochemisch durchgefuhrt, ohne die Notwendigkeit von Metallen und Reagenzien. Ein breites Spektrum an Biphenyldiaminen konnte hergestellt werden. Die besten Resultate wurden mit Glaskohlenstoff als Anodenmaterial erhalten. Die elektrochemische Umsetzung kann problemlos in einer ungeteilten Zelle bei leicht erhohten Temperaturen durchgefuhrt werden. Auserdem wurden gebrauchliche, auf Carbonsauren basierende, Schutzgruppen verwendet, die nach der Kreuzkupplung unter milden Bedingungen selektiv abgespalten werden konnen. Auf diese Weise erhalt man schnell und effizient Zugan…
Titelbild: Metall- und reagensfreie hochselektive anodische Kreuzkupplung von Phenolen (Angew. Chem. 20/2014)
2014
ChemInform Abstract: Selective Synthesis of Partially Protected Nonsymmetric Biphenols by Reagent- and Metal-Free Anodic Cross-Coupling Reaction.
2016
The oxidative cross-coupling of aromatic substrates without the necessity of leaving groups or catalysts is described. The selective formation of partially protected nonsymmetric 2,2'-biphenols via electroorganic synthesis was accomplished with a high yield of isolated product. Since electric current is employed as the terminal oxidant, the reaction is reagent-free; no reagent waste is generated as only electrons are involved. The reaction is conducted in an undivided cell, and is suitable for scale-up and inherently safe. The implementation of O-silyl-protected phenols in this transformation results in both significantly enhanced yields and higher selectivity for the desired nonsymmetric 2…
Reagent- and Metal-Free Anodic C-C Cross-Coupling of Aniline Derivatives.
2017
The dehydrogenative cross-coupling of aniline derivatives to 2,2′-diaminobiaryls is reported. The oxidation is carried out electrochemically, which avoids the use of metals and reagents. A large variety of biphenyldiamines were thus prepared. The best results were obtained when glassy carbon was used as the anode material. The electrosynthetic reaction is easily performed in an undivided cell at slightly elevated temperature. In addition, common amine protecting groups based on carboxylic acids were employed that can be selectively removed under mild conditions after the cross-coupling, which provides quick and efficient access to important building blocks featuring free amine moieties.
CCDC 980571: Experimental Crystal Structure Determination
2014
Related Article: Bernd Elsler, Dieter Schollmeyer, Katrin Marie Dyballa, Robert Franke and Siegfried R. Waldvogel|2014|Angew.Chem.,Int.Ed.|53|5210|doi:10.1002/anie.201400627
CCDC 980570: Experimental Crystal Structure Determination
2014
Related Article: Bernd Elsler, Dieter Schollmeyer, Katrin Marie Dyballa, Robert Franke and Siegfried R. Waldvogel|2014|Angew.Chem.,Int.Ed.|53|5210|doi:10.1002/anie.201400627
CCDC 980563: Experimental Crystal Structure Determination
2014
Related Article: Bernd Elsler, Dieter Schollmeyer, Katrin Marie Dyballa, Robert Franke and Siegfried R. Waldvogel|2014|Angew.Chem.,Int.Ed.|53|5210|doi:10.1002/anie.201400627
CCDC 980565: Experimental Crystal Structure Determination
2014
Related Article: Bernd Elsler, Dieter Schollmeyer, Katrin Marie Dyballa, Robert Franke and Siegfried R. Waldvogel|2014|Angew.Chem.,Int.Ed.|53|5210|doi:10.1002/anie.201400627
CCDC 980569: Experimental Crystal Structure Determination
2014
Related Article: Bernd Elsler, Dieter Schollmeyer, Katrin Marie Dyballa, Robert Franke and Siegfried R. Waldvogel|2014|Angew.Chem.,Int.Ed.|53|5210|doi:10.1002/anie.201400627
CCDC 980564: Experimental Crystal Structure Determination
2014
Related Article: Bernd Elsler, Dieter Schollmeyer, Katrin Marie Dyballa, Robert Franke and Siegfried R. Waldvogel|2014|Angew.Chem.,Int.Ed.|53|5210|doi:10.1002/anie.201400627
CCDC 980568: Experimental Crystal Structure Determination
2014
Related Article: Bernd Elsler, Dieter Schollmeyer, Katrin Marie Dyballa, Robert Franke and Siegfried R. Waldvogel|2014|Angew.Chem.,Int.Ed.|53|5210|doi:10.1002/anie.201400627
CCDC 980566: Experimental Crystal Structure Determination
2014
Related Article: Bernd Elsler, Dieter Schollmeyer, Katrin Marie Dyballa, Robert Franke and Siegfried R. Waldvogel|2014|Angew.Chem.,Int.Ed.|53|5210|doi:10.1002/anie.201400627
CCDC 980567: Experimental Crystal Structure Determination
2014
Related Article: Bernd Elsler, Dieter Schollmeyer, Katrin Marie Dyballa, Robert Franke and Siegfried R. Waldvogel|2014|Angew.Chem.,Int.Ed.|53|5210|doi:10.1002/anie.201400627