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Dichiral [4.4.3.0 1,5 ]tridecane copper(II) cluster derived from a tripodal ligand having unsymmetrical podands and the linker: Synthesis, structure, surface grafting and catalytic aspects
Author(s) -
Singh Hemant,
Taya Navneet,
Agarwal Jyoti,
Singh Raghubir,
Kaur Varinder
Publication year - 2021
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.6075
Subject(s) - chemistry , copper , catalysis , infrared spectroscopy , fourier transform infrared spectroscopy , crystallography , tripodal ligand , covalent bond , ligand (biochemistry) , scanning electron microscope , amine gas treating , crystal structure , stereochemistry , organic chemistry , biochemistry , physics , receptor , quantum mechanics
Pseudo‐atranes have a significant role in catalysis; however, obtaining chiral pseudo‐atranes for covalent functionalization of heterogeneous catalytic surfaces is very challenging. Herein, synthesis of a chiral tripodal amine [N{CH (CH 2 Ph)CH 2 OH}{CH 2 (4BrC 6 H 3 OH)}{CH 2 (2CHO4MeC 6 H 2 OH)}] ( 1 ) and a dichiral [4.4.3.0 1,5 ]tridecane copper(II) cluster, that is, (Cu[N{CH (CH 2 Ph)CH 2 OH}{CH 2 (4BrC 6 H 3 O)}{CH 2 (2CHO4MeC 6 H 2 O)}]) 2 ( 2 ) is described. The compounds are characterized by elemental analyses, Fourier transform infrared (FT‐IR) spectroscopy, mass spectrometry and single‐crystal X‐ray crystallography (for 2 ). The compound 2 is the first example of chiral pseudo‐copper(II)atrane in which three unsymmetrical arms (two phenolic and a chiral ethanolic arm) are fused via CuN transannular bond. The free CHO group present in one of the tricyclic arms of the 2 is tested as a linker to load it on 3‐aminopropyltriethoxysilane‐functionalized magnetic nanosilica for catalytic applications. The loading of 2 on magnetic nanosilica through CHO was confirmed by FT‐IR spectroscopy, and the 2 ‐loaded magnetic nanosilica ( Fe 3 O 4 @SiO 2 /2 ) was characterized by powder X‐ray diffraction, vibrating sample magnetometry, scanning electron microscopy, energy‐dispersive X‐ray spectroscopy and elemental mapping. The Fe 3 O 4 @SiO 2 /2 was found highly efficient, retrievable, eco‐friendly and green catalyst for obtaining β‐amino alcohols in excellent yields in an aqueous medium. Overall, present work is the first report on synthetic, structural and catalytic aspects of dichiral cluster of copper(II)atrane possessing unsymmetrical tricyclic arms.