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钯催化 δ-酮腈与芳基硼酸的串联反应:吡啶的合成。

Palladium-Catalyzed Cascade Reactions of δ-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines.

机构信息

College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China.

School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, P. R. China.

出版信息

ACS Comb Sci. 2020 Mar 9;22(3):114-119. doi: 10.1021/acscombsci.9b00198. Epub 2020 Feb 14.

Abstract

This study presents the first example of the Pd-catalyzed cascade reactions of 5-oxohexanenitrile with arylboronic acids, affording important synthon 2-methylpyridines that can be further translated through C(sp)-H functionalization to construct pyridine derivatives. Furthermore, this chemistry allows 5-oxo-5-arylpentanenitrile to react with arylboronic acids to provide unsymmetrical 2,6-diarylpyridines. This protocol paves the way for the practical and atom economical syntheses of valuable pyridines with broad functional groups in moderate to excellent yields under mild conditions.

摘要

本研究展示了首例钯催化的 5-氧代己腈与芳基硼酸的级联反应,得到了重要的合成子 2-甲基吡啶,它可以通过 C(sp^3)-H 官能化进一步转化为构建吡啶衍生物。此外,这种化学方法允许 5-氧代-5-芳基戊腈与芳基硼酸反应,提供不对称的 2,6-二芳基吡啶。该方案为在温和条件下以中等至优异的收率,通过实用和原子经济性的方法合成具有广泛官能团的有价值的吡啶开辟了道路。

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