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有机催化合成(Het)联芳骨架 通过 2-吡啶酮衍生物的光诱导分子内/分子间 C(sp)-H 芳基化反应

Organocatalytic synthesis of (Het)biaryl scaffolds photoinduced intra/intermolecular C(sp)-H arylation by 2-pyridone derivatives.

机构信息

TCG Lifesciences Pvt. Ltd., BN-7, Sector V, Salt Lake City, Kolkata-700091, India.

Department of Chemistry, University of North Bengal, Darjeeling, 734013, India.

出版信息

Org Biomol Chem. 2021 Dec 22;20(1):208-218. doi: 10.1039/d1ob01798e.

Abstract

A unique ,-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcased the construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.

摘要

一种独特的、双齿配体 6-氧代-1,6-二氢-吡啶酮-2-羧酸二甲酰胺(L1),可以在室温下通过 UV 照射,催化未活化芳环的直接 C(sp)-H(内/间)芳基化反应,从而快速构建(Het)联芳基骨架。该方案可以容忍各种官能团和取代模式,以中等至优异的收率得到目标产物。还进行了机理研究,以更好地理解反应途径。此外,该统一方法的合成适用性已通过构建生物相关的 4-喹诺酮、三环内酰胺和脒衍生物得到展示。

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