通过铜催化的 CF-炔酮和乙烯基叠氮化物的环化反应，区域选择性合成 2,4-二芳基-6-三氟甲基化吡啶。

Regioselective Synthesis of 2,4-Diaryl-6-trifluoromethylated Pyridines through Copper-Catalyzed Cyclization of CF-Ynones and Vinyl Azides.

机构信息

School of Medicine, Huaqiao University, Quanzhou 362021, P.R. China.

College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, P.R. China.

出版信息

J Org Chem. 2021 May 7;86(9):6423-6432. doi: 10.1021/acs.joc.1c00275. Epub 2021 Apr 27.

DOI:10.1021/acs.joc.1c00275

PMID:33905254

Abstract

A novel copper-catalyzed cyclization of readily available vinyl azides with CF-ynones is steadily achieved under mild conditions to furnish the versatile 2,4-diaryl-6-trifluoromethylated pyridine products, which are of great interest in medicinal chemistry. The generation of the vinyl iminophosphorane intermediates from vinyl azides through the Staudinger-Meyer reaction ensures the subsequent 1,4-addition process with CF-ynones in this transformation.

摘要

在温和条件下，通过铜催化 readily available vinyl azides 与 CF-ynones 的新型环化反应，稳定地得到多功能的 2,4-二芳基-6-三氟甲基化吡啶产物，这在药物化学中具有重要的意义。通过 Staudinger-Meyer 反应从 vinyl azides 生成 vinyl iminophosphorane 中间体，确保了在这个转化中与 CF-ynones 的后续 1,4-加成过程。