- Electrochemical Synthesis of Biaryls via Oxidative Intramolecular Coupling of Tetra(hetero)arylborates
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We report herein versatile, transition metal-free and additive-free (hetero)aryl-aryl coupling reactions promoted by the oxidative electrocoupling of unsymmetrical tetra(hetero)arylborates (TABs) prepared from ligand-exchange reactions on potassium trifluoroarylborates. Exploiting the power of electrochemical oxidations, this method complements the existing organoboron toolbox. We demonstrate the broad scope, scalability, and robustness of this unconventional catalyst-free transformation, leading to functionalized biaryls and ultimately furnishing drug-like small molecules, as well as late stage derivatization of natural compounds. In addition, the observed selectivity of the oxidative coupling reaction is related to the electronic structure of the TABs through quantum-chemical calculations and experimental investigations.
- Music, Arif,Baumann, Andreas N.,Spie?, Philipp,Plantefol, Allan,Jagau, Thomas C.,Didier, Dorian
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supporting information
p. 4341 - 4348
(2020/03/04)
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- Sensitized photografting of diazonium salts by visible light.
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Visible irradiation of a gold surface dipped into a solution of diversely substituted aryldiazonium salts in the presence of a photosensitizer (Ru(bipy)32+ or eosinY) leads to a modification of the surface by attached aryl groups. A grafted nanometer thick polyphenylene film is obtained. The reaction is extended to a polyvinylchloride (PVC) surface. The mechanism proposed for the formation of this film involves the formation of an aryl radical that reacts with the surface and then with the first grafted aryl group. The film is characterized by infrared reflection absorption spectroscopy (IRRAS), X-ray photoelectron spectroscopy (XPS), water contact angles, and ellipsometry.
- Bouriga, Meriem,Chehimi, Mohamed M.,Combellas, Catherine,Decorse, Philippe,Kanoufi, Frederic,Deronzier, Alain,Pinson, Jean
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- 1,4-Difluoro-2,5-dimethoxybenzene as a precursor for iterative double benzyne-furan Diels-Alder reactions
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(Chemical Equation Presented) The use of 1,4-difluoro-2,5-dimethoxybenzene as a novel precursor for iterative two-directional benzyne-furan Diels-Alder reactions, using a range of 2- and 3-substituted furans, is reported. Substituted oxabenzonorbornadiene
- Morton, Gillian E.,Barrett, Anthony G. M.
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p. 3525 - 3529
(2007/10/03)
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