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Direct Arylation of N‐Heteroarenes with Aryldiazonium Salts by Photoredox Catalysis in Water
Author(s) -
Xue Dong,
Jia ZhiHui,
Zhao CongJun,
Zhang YanYan,
Wang Chao,
Xiao Jianliang
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304120
Subject(s) - chemistry , photoredox catalysis , catalysis , thiazole , aryl , solvent , aqueous solution , pyrazine , pyridazine , combinatorial chemistry , formic acid , photosensitizer , substrate (aquarium) , environmentally friendly , green chemistry , pyridine , photochemistry , organic chemistry , photocatalysis , reaction mechanism , alkyl , oceanography , geology , ecology , biology
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 ]Cl 2 ⋅ 6 H 2 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.