title: Direct arylation of N-heteroarenes with aryldiazonium salts by photoredox catalysis in water.
abstract: 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.
authors: Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062 (China). Xuedong_welcome@snnu.edu.cn.
authors: Dong
authors: D
authors: Xue
authors: Zhi-Hui
authors: ZH
authors: Jia
authors: Cong-Jun
authors: CJ
authors: Zhao
authors: Yan-Yan
authors: YY
authors: Zhang
authors: Chao
authors: C
authors: Wang
authors: Jianliang
authors: J
authors: Xiao
mesh_terms: D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D055668:Photochemical Processes; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D012492:Salts / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D056831:Coordination Complexes; D003979:Diazonium Compounds; D006571:Heterocyclic Compounds; D011725:Pyridines; D012492:Salts; D012997:Solvents; D014867:Water; D012428:Ruthenium
keywords: N-heteroarenes; aryldiazonium salts; cross-coupling; green chemistry; photoredox catalysis; water