Homoleptic and heteroleptic Zn(ii) selone catalysts for thioetherification of aryl halides without scrubbing oxygen

Vaddamanu, Moulali and Velappan, Kavitha and Prabusankar, Ganesan (2020) Homoleptic and heteroleptic Zn(ii) selone catalysts for thioetherification of aryl halides without scrubbing oxygen. New Journal of Chemistry, 44 (9). pp. 3574-3583. ISSN 1144-0546

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Abstract

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 a one-pot reaction between the 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 a distorted tetrahedral geometry. Besides, 1-5 were employed as catalysts in the thioetherification of aryl halides. The first zinc(ii) catalyst-mediated thioetherification of aryl halides without scrubbing oxygen was demonstrated. Catalysts 1-5 are 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 to two selone ligands is much more catalytically active than that attached to four selone ligands.

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IITH Creators:
IITH CreatorsORCiD
Vaddamanu, MoulaliUNSPECIFIED
Velappan, KavithaUNSPECIFIED
Prabusankar, GanesanUNSPECIFIED
Item Type: Article
Uncontrolled Keywords: Article; carbon nuclear magnetic resonance; catalyst; chemical structure; cross coupling reaction; density functional theory; elemental analysis; etherification; Fourier transform infrared spectroscopy; priority journal; proton nuclear magnetic resonance; solvent extraction; synthesis; thioetherification; X ray crystallography; X ray diffraction
Subjects: Chemistry
Chemistry > Inorganic chemistry
Chemistry > Organic chemistry
Chemical Engineering
Divisions: Department of Chemistry
Depositing User: . LibTrainee 2021
Date Deposited: 21 Jun 2021 10:32
Last Modified: 21 Jun 2021 10:32
URI: http://raiith.iith.ac.in/id/eprint/7962
Publisher URL: http://doi.org/10.1039/c9nj05818d
OA policy: https://v2.sherpa.ac.uk/id/publication/18027
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