A Robust Three-Step Telescoped Synthesis of Electron- Deficient Amide Substituted Arylboronic Acids

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• 作者：Jason Zhu ; Thomas M. Razler ; Zhongmin Xu ; David A. Conlon ; Eric W. Sortore ; Alan W. Fritz ; Roman Demerzhan ; Jason T. Sweeney
• 刊名：Organic Process Research & Development
• 出版年：2011
• 出版时间：March 18, 2011
• 年：2011
• 卷：15
• 期：2
• 页码：438-442
• 全文大小：811K
• 年卷期：v.15,no.2(March 18, 2011)
• ISSN：1520-586X

文摘

A robust three-step telescoped process for the preparation of electron-deficient amide-substituted arylboronic acids from readily available bromobenzoic acids has been developed. An EDC-HOBT-promoted amide formation of a bromobenzoic acid was followed by subjection of the product stream to a palladium-mediated cross-coupling with B₂(pin)₂. The resultant mixture of the arylboronate ester and arylboronic acid was directly treated with NaIO₄, followed by a heptane鈭扢eTHF crystallization, to cleanly afford the corresponding arylboronic acid in good yield. This general procedure was used to synthesize electron-deficient amide-substituted arylboronic acids with a diverse array of electron-withdrawing substituents.