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钯催化β-酮腈与芳基硼酸和二甲基亚砜的串联反应:在多组分合成多取代吡啶中的应用

Palladium-Catalyzed Tandem Reaction of β-Ketonitriles with Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent Synthesis of Poly-Substituted Pyridines.

作者信息

Zeng Ge, Wang Shiyan, Han Wantong, Zhou Honggui, Liu Min, Li Yifei, Liu Miaochang, Chen Jiuxi, Li Renhao

机构信息

State Key Laboratory of Macromolecular Drugs and Large-Scale Manufacturing, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, P. R. China.

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

出版信息

J Org Chem. 2025 Jan 24;90(3):1388-1399. doi: 10.1021/acs.joc.4c02778. Epub 2025 Jan 9.

Abstract

The Pd-catalyzed multicomponent tandem reaction of β-ketonitriles, arylboronic acids and DMSO was efficiently developed, enabling access to a variety of poly substituted pyridines. The protocol shows excellent chemoselectivity, generating nicotinonitriles or symmetrical tetrasubstituted pyridines under different conditions by tandem cyclization of enaminone intermediates with β-ketonitriles or enolates, respectively, and does not require extra ammonias. This method boasts notable advantages, such as the use of commercially available or easily prepared substrates, simple conditions, a broad substrate scope, and good functional group tolerance.

摘要

钯催化的β-酮腈、芳基硼酸和二甲基亚砜的多组分串联反应得到了有效开发,能够合成多种多取代吡啶。该方法具有出色的化学选择性,通过烯胺酮中间体分别与β-酮腈或烯醇盐串联环化,在不同条件下生成烟腈或对称的四取代吡啶,且无需额外的氨。此方法具有显著优势,例如使用市售或易于制备的底物、条件简单、底物范围广以及良好的官能团耐受性。

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