Direct Arylation of N-Heteroarenes with Aryldiazonium Salts by Photoredox Catalysis in Water
| Autor: | Jianliang Xiao, Zhi-Hui Jia, Dong Xue, Cong-Jun Zhao, Yanyan Zhang, Chao Wang |
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| Rok vydání: | 2014 |
| Předmět: |
Green chemistry
Aqueous solution Molecular Structure Pyrazine Pyridines Organic Chemistry Water Photoredox catalysis Diazonium Compounds General Chemistry Photochemical Processes Combinatorial chemistry Ruthenium Catalysis Pyridazine Solvent chemistry.chemical_compound chemistry Coordination Complexes Heterocyclic Compounds Pyridine Solvents Organic chemistry Salts Thiazole |
| Zdroj: | Chemistry - A European Journal. 20:2960-2965 |
| ISSN: | 0947-6539 |
| DOI: | 10.1002/chem.201304120 |
| Popis: | A highly effective visible light-promoted "radical-type" coupling of N-heteroarenes with aryldiazonium salts in water has been developed. The reaction proceeds at room temperature with [Ru(bpy)3 ]Cl2 ⋅6 H2 O as a photosensitizer and a commercial household light bulb as a light source. Pyridine and a variety of substituted pyridines are effective substrates under these reaction conditions, and only monosubstituted products are formed with different regioselectivities. Using aqueous formic acid as solvent, an array of xanthenes, thiazole, pyrazine, and pyridazine are compatible with this new arylation approach. The broad substrate scope, mild reaction conditions, and use of water as reaction solvent make this procedure a practical and environmentally friendly method for the synthesis of compounds containing aryl-heteroaryl motifs. |
| Databáze: | OpenAIRE |
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