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通过 Co(III)催化和 DMSO 参与的苯胺与炔烃的 C-H 活化/环化反应直接合成喹啉。

Direct Synthesis of Quinolines via Co(III)-Catalyzed and DMSO-Involved C-H Activation/Cyclization of Anilines with Alkynes.

机构信息

College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University , Nanyang 473061, China.

Key Laboratory of Molecular Clinical Pharmacology & Fifth Affiliated Hospital, Guangzhou Medical University , Guangzhou, Guangdong 511436, China.

出版信息

Org Lett. 2018 Feb 2;20(3):566-569. doi: 10.1021/acs.orglett.7b03673. Epub 2018 Jan 11.

Abstract

A unique Co(III)-catalyzed and DMSO-involved C-H activation/cyclization of simple, cheap, and easily available anilines with alkynes for direct and highly efficient synthesis of privileged quinolines with exclusive regioselectivity and broad substrate/functional group tolerance and in good to excellent yields, where DMSO was employed as both the solvent and the C building block of quinoline products, is reported. Mechanistic experiments revealed that the versatile reaction might employ the 2-vinylbenzenamine species as the active intermediate.

摘要

报道了一种独特的 Co(III)催化、DMSO 参与的简单、廉价且易得的苯胺与炔烃的 C-H 活化/环化反应,用于直接、高效地合成具有独特区域选择性和广泛底物/官能团耐受性的喹啉,产率良好至优秀,其中 DMSO 既作为溶剂又作为喹啉产物的 C 构建块。机理实验表明,该多功能反应可能采用 2-乙烯基苯胺物种作为活性中间体。

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