1702-67-6Relevant articles and documents
The reaction pattern of the MoCl5-mediated oxidative aryl-aryl coupling
Waldvogel, Siegfried R.
, p. 622 - 624 (2002)
The oxidative coupling of electron rich aryls by molybdenum pentachloride is reported. The stoichiometry of the coupling reaction reveals that MoCl5 is a single electron acceptor. Interestingly, the 1,2-dialkoxy substitution pattern is pivotal for the arylaryl coupling.
Anodic oxidation of hexamethoxybiphenyls into either stable cation radical salt or spiro(fluorene-9,1′-cyclohexadienones)
Douadi, Tahar,Cariou, Michel,Simonet, Jacques
, p. 4449 - 4456 (1996)
Three symmetrically substituted hexamethoxybiphenyls were subjected to electrooxidation at a platinum anode. 2,2′,4,4′,5,5′-hexamethoxybiphenyl led to the stable cation radical salt expected, whereas 3,3′,4,4′,5,5′-hexamethoxybiphenyl and 2,2′,3,3′,4,4′-h
Source of Selectivity in Oxidative Cross-Coupling of Aryls by Solvent Effect of 1,1,1,3,3,3-Hexafluoropropan-2-ol
Elsler, Bernd,Wiebe, Anton,Schollmeyer, Dieter,Dyballa, Katrin M.,Franke, Robert,Waldvogel, Siegfried R.
, p. 12321 - 12325 (2015)
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 to phenol-phenol as well as phenol-aniline cross-coupling. This driving force for selectivity in oxidative coupling might also explain previous findings using HFIP and hypervalent iodine reagents. A remarkable and tunable solvent effect is responsible for the highly selective cross-coupling of phenols with arenes, phenols or aniline derivatives (see scheme). The solvent mixture allows the decoupling of nucleophilicity and oxidation potential to some extent.
Active Molybdenum-Based Anode for Dehydrogenative Coupling Reactions
Beil, Sebastian B.,Müller, Timo,Sillart, Sydney B.,Franzmann, Peter,Bomm, Alexander,Holtkamp, Michael,Karst, Uwe,Schade, Wolfgang,Waldvogel, Siegfried R.
supporting information, p. 2450 - 2454 (2018/02/09)
A new and powerful active anode system that can be operated in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) has been discovered. In HFIP the molybdenum anode forms a compact, conductive, and electroactive layer of higher-valent molybdenum species. This system can replace powerful but stoichiometrically required MoV reagents for the dehydrogenative coupling of aryls. This electrolytic reaction is more sustainable and allows the conversion of a broad scope of activated arenes.
Photocatalytic Phenol–Arene C–C and C–O Cross-Dehydrogenative Coupling
Eisenhofer, Anna,Hioe, Johnny,Gschwind, Ruth M.,K?nig, Burkhard
supporting information, p. 2194 - 2204 (2017/04/24)
Phenol-containing nonsymmetrical biaryls play an important role in natural-product synthesis, as ligands in metal catalysis, and in organic functional materials. Their synthesis through cross-coupling reactions by two-fold direct C–H activation are import
