Azidosubstituted arylboronic acids: synthesis and Suzuki–Miyaura cross-coupling reactions

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• 作者：Sergey I. Sviridov ; Andrei A. Vasil'ev ; Natalia L. Sergovskaya ; Marina V. Chirskaya and Sergey V. Shorshnev
• 关键词：Azides ; Boronic acids ; Cross-coupling ; 2 ; 3-Dihydrobenzo[ ; b] ; furans ; Nitriles
• 刊名：Tetrahedron
• 出版年：2006
• 出版时间：13 March 2006
• 年：2006
• 卷：62
• 期：11
• 页码：2639-2647
• 全文大小：154 K

文摘

Arylboronic acids having a remote azido group were prepared from the corresponding azidosubstituted aryl bromides via lithiation and treatment with trialkyl borates. Preparative yields were achieved when the starting aryl bromides possessed ortho-alkoxy groups, which would stabilize the intermediate aryllithium species. Conventional Suzuki cross-coupling of the arylboronic acids proceeded generally well with retention of azido group; however, sometimes azidomethyl fragment underwent oxidative transformation into a nitrile.