有氧铜介导的多米诺反应合成 3-(三氟甲基硒基)吲哚。

An aerobic copper-mediated domino process for the synthesis of 3-(trifluoromethylseleno)indoles.

机构信息

Key Laboratory of Molecule Synthesis and Function Discovery, and Fujian Provincial Key Laboratory of Electrochemical Energy Storage Materials, College of Chemistry, Fuzhou University, Fuzhou, 350108, China.

Fujian Engineering Research Center of New Chinese lacquer Material, Ocean College, Minjiang University, Fuzhou, 350108, China.

出版信息

Org Biomol Chem. 2022 Mar 9;20(10):2115-2120. doi: 10.1039/d2ob00063f.

DOI:10.1039/d2ob00063f

PMID:35212348

Abstract

An aerobic copper-mediated domino reaction for the synthesis of 3-(trifluoromethylseleno)indoles by trifluoromethylselenolation of -Ts 2-alkynylaniline with [(bpy)CuSeCF] is reported. This reaction proceeds through sequential oxidation, alkyne coordination, and deprotonation followed by reductive elimination. This mild and robust method is highly functional group tolerant and provides straightforward access to 3-(trifluoromethylseleno)indoles in moderate to good yields.

摘要

报道了一种有氧铜介导的级联反应，通过[(bpy)CuSeCF]与 -Ts 2-炔基苯胺的三氟甲基硒化反应合成 3-(三氟甲基硒基)吲哚。该反应通过顺序氧化、炔烃配位、脱质子化和还原消除进行。这种温和而强大的方法对官能团具有高度耐受性，并能以中等至良好的收率直接获得 3-(三氟甲基硒基)吲哚。