Synthesis of 2,3-Bis(trifluoromethylseleno) Indoles through an Oxidative Copper-Mediated Domino Reaction

Hui Wang; Yunfei Yao; Zipeng Zhang; Yangjie Huang; Zhiqiang Weng

doi:10.1021/acs.joc.1c03156

Synthesis of 2,3-Bis(trifluoromethylseleno) Indoles through an Oxidative Copper-Mediated Domino Reaction

J Org Chem. 2022 Mar 4;87(5):3605-3612. doi: 10.1021/acs.joc.1c03156. Epub 2022 Feb 15.

Authors

Hui Wang^{1

2}, Yunfei Yao², Zipeng Zhang², Yangjie Huang¹, Zhiqiang Weng^{1

2}

Affiliations

¹ Fujian Engineering Research Center of New Chinese Lacquer Material, Ocean College, Minjiang University, Fuzhou 350108, China.
² 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.

PMID: 35166556
DOI: 10.1021/acs.joc.1c03156

Abstract

An oxidative copper-mediated double trifluoromethylselenolation of terminal 2-alkynylanilines using [(bpy)CuSeCF₃]₂ is reported, providing a moderately efficient and convenient approach to 2,3-bis(trifluoromethylseleno)indoles. Mechanistic studies show that a cascade sequence of oxidation, trifluoromethylselenolation, 5-endo-dig cyclization, and elimination is involved in this transformation.