One-Pot C鈥揘/C鈥揅 Cross-Coupling of Methyliminodiacetic Acid Boronyl Arenes Enabled by Protective Enolization

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• 作者：Jonathan E. Grob ; Michael A. Dechantsreiter ; Ritesh B. Tichkule ; Michael K. Connolly ; Ayako Honda ; Ronald C. Tomlinson ; Lawrence G. Hamann
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：November 2, 2012
• 年：2012
• 卷：14
• 期：21
• 页码：5578-5581
• 全文大小：287K
• 年卷期：v.14,no.21(November 2, 2012)
• ISSN：1523-7052

文摘

Iterative cross-coupling is a highly efficient and versatile strategy for modular construction in organic synthesis, though this has historically been demonstrated solely in the context of C鈥揅 bond formation. A C鈥揘 cross-coupling of haloarene methyliminodiacetic acid (MIDA) boronates with a wide range of aromatic and aliphatic amines is reported. Successful cross-coupling of aliphatic amines was realized only through protective enolization of the MIDA group. This reaction paradigm was subsequently utilized to achieve a one-pot C鈥揘/C鈥揅 cross-coupling sequence.