Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki-Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters

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• 作者：Zahid Hassan^a ; ^b ; Munawar Hussain^a ; Alexander Villinger^a ; Peter Langer^a ; ^b ; ^{peter.langer@uni-rostock.de}
• 关键词：Catalysis ; Palladium ; Tetralone ; Suzuki&ndash ; Miyaura reaction ; Naphthalene ; Naphthaquinones ; Chemoselectivity
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：5 August, 2012
• 卷：68
• 期：31
• 页码：6305-6313
• 文件大小：801 K

摘要

Chemoselective Suzuki-Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the triflate group is electronically more deficient by the presence of a neighbouring acetyl group.