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Homoleptic and Heteroleptic Zn(II) Selone Catalysts for Thioetherification of Aryl Halides without Scrubbing Oxygen

Abstract

The five new mononuclear tetra coordinated zinc(II) selones, [Zn(L1)2Cl2] (1), [Zn(L1)2Br2] (2), [{Zn(L2)4}{BF4}2] (3), [{Zn(L2)4}{ClO4}2] (4), and [Zn(L2)2Br2] (5) have been isolated from one-pot reaction between corresponding zinc(II) salt and selone ligand, 1-methyl 3-naphthylmethylimidazoline-2-selone (L1) or 1-isopropyl 3-methylimidazoline-2-selone (L2). All these complexes were characterized by CHN analysis, FT-IR, NMR studies, and single-crystal X-ray crystallography techniques. The Zn(II) center in 1-5 exhibits the distorted tetrahedral geometries. Besides, 1-5 were employed as catalysts in thioetherification of aryl halide. The first zinc(II) catalyst mediated thioetherification of aryl halide without scrubbing oxygen was demonstrated. The catalysts 1-5 have been highly active towards the cross-coupling reaction between aryl halides and thiophenols. The catalytic ability of 1-5 was explored in THF, Toluene, and CH3CN solvents with different bases such as K2CO3, Cs2CO3, and NaOtBu. Interestingly, the zinc(II) center attached with two selone ligands is much more catalytically active than four selone ligands.

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Supplementary files

Article information


Submitted
22 Nov 2019
Accepted
07 Jan 2020
First published
08 Jan 2020

New J. Chem., 2020, Accepted Manuscript
Article type
Paper

Homoleptic and Heteroleptic Zn(II) Selone Catalysts for Thioetherification of Aryl Halides without Scrubbing Oxygen

M. Vaddamanu, K. Velappan and P. Ganesan, New J. Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9NJ05818D

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