Copper catalyzed Gomberg–Buchmann–Hey reaction using aryldiazonium tosylate

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• 作者：Ganesh U. Chaturbhuj^a ; Krishnacharya G. Akamanchi^a ; ^{kgap@rediffmail.com"" rel=""nofollow}
• 关键词：Gomberg– ; Buchmann– ; Hey reaction ; Aryldiazonium tosylate ; Cross coupling ; Copper catalyst ; Biaryls
• 刊名：Tetrahedron Letters
• 出版年：2011
• 出版时间：21 September 2011
• 年：2011
• 卷：52
• 期：38
• 页码：4950-4953
• 全文大小：965 K

文摘

Copper catalyzed modification of Gomberg–Bachmann–Hey reaction to synthesize symmetrical/unsymmetrical biaryls via diazotization of anilines with p-TSA and NaNO₂ system at 50 °C, in aromatic liquids as solvents and second partners was successfully developed. Aniline and 3-nitronaniline gave biphenyl and 3-nitrobiphenyl, respectively, with moderate yields. All para-substituted anilines gave comparatively higher yields while in the other cases including ortho-substituted anilines yields were lower. Except anilines with o-NHCOCH₃ and o-CONH₂ which gave symmetrical biaryls, all others gave selectively unsymmetrical biaryls.