- Aryl Diazonium Salts: Powerful Arylating Agents for Catellani-Typeortho-Arylation
-
The Catellani reaction provides an efficient synthetic approach to polyfunctionalized arenes. However, the selectiveortho-arylating reagents employed in these reactions have been strictly limited to activated bromoarenes. As demonstrated in this work, aryl diazonium salts bearing both electron-donating and electron-withdrawing substituents, after in situ transformations with KI into the corresponding iodoarenes, were efficient arylating reagents for Catellani typeortho-arylation approaches.
- Fu, Ying,Guo, Liang-Liang,Zhang, Yu-Xia
-
supporting information
p. 17437 - 17444
(2021/12/02)
-
- Sensitized photografting of diazonium salts by visible light.
-
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
-
-
- Long-chain Phenols. Part 16. A Novel Synthesis of Homologous Orsellinic Acids and their Methyl Ethers
-
By the novel reaction of 3,5-dimethoxyfluorobenzene with n-alkyl-lithium compounds, followed by carbonation, homologous orsellinic acid dimethyl ethers (6-alkyl-2,4-dimethoxybenzoic acids) have been obtained.The reactions proceeded best with the homologues of methyl-lithium.These reactions are considered to occur by way of 3,5-dimethoxybenzyne. 2,4-Dimethoxyfluorobenzene did not form an aryne but gave 3-fluoro-2,6-dimethoxybenzoic acid instead.Decomposition with water of alkyl-lithium reaction mixtures from 3,5-dimethoxyfluorobenzene yielded 5-n-alkylresorcinol dimethyl ethers.Demethylaton of 6-alkyl-2,4-dimethoxybenzoic acids with boron trichloride proceeded partially and selectively to give the 6-alkyl-2-hydroxy-4-methoxybenzoic acids, and completely with aluminium chloride to give the homologous orsellinic acids.Boron tribromide was less effective, but readily gave the 5-alkyl resorcinols from the corresponding dimethyl ethers.
- Durrani, Aziz A.,Tyman, John H. P.
-
p. 1658 - 1666
(2007/10/02)
-