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Synthesis of a new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: Crystal Structure, DFT study and catalytic investigation of Palladium and Nickel complexes towards deacylative sulfenylation of active methylene and regioselective 3-sulfenylation of indoles via thiouronium salt formation

Abstract

A series of Ni(II), Cu(II), Co(II), and Pd(II) complexes have been synthesized with a chelating Schiff base ligand coordinated to metal center with ONS donor atoms. The ligand and complexes are characterized with elemental analysis and spectroscopic techniques like FT-IR, 1H-NMR, UV–Visible spectroscopy. The single crystal structure of Pd(II) complex is obtained by X-ray diffraction analysis and exhibits slightly distorted square planar geometry. The structure is optimized by DFT; TD-DFT calculation to elaborate the electronic structure and NBO for charge distribution analysis of the Pd(II) complex. The synthesized Pd(II) and Ni(II) complexes as catalyst have been investigated in C-S cross coupling of indoles and active methylenes. The metal propelled regioselective transformation afforded 3-sulfenylated indoles while, β-diketones favored deacylated monosulfenyl ketones in excellent yield via thiouronium salt formation. Pd(II) complex displays slightly better reactivity whereas Ni(II) complex is cost-efficient. The method is fast, easy to handle and cost effective in terms of high reactivity of catalyst, use of non-toxic solvent, and cheaper aryl halides and thiourea replace conventional sulfur sources, providing a practical access to organic transformations.

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Publication details

The article was received on 07 Dec 2017, accepted on 13 Feb 2018 and first published on 14 Feb 2018


Article type: Paper
DOI: 10.1039/C7DT04635A
Citation: Dalton Trans., 2018, Accepted Manuscript
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    Synthesis of a new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: Crystal Structure, DFT study and catalytic investigation of Palladium and Nickel complexes towards deacylative sulfenylation of active methylene and regioselective 3-sulfenylation of indoles via thiouronium salt formation

    N. Devi, K. Sarma, R. Rahaman and P. Barman, Dalton Trans., 2018, Accepted Manuscript , DOI: 10.1039/C7DT04635A

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