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Electrochemistry of substituted salen complexes of nickel(II): Nickel(I)-catalyzed reduction of alkyl and acetylenic halides

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Title: Electrochemistry of substituted salen complexes of nickel(II): Nickel(I)-catalyzed reduction of alkyl and acetylenic halides
Authors: Foley, Matthew P.1, Du, Peng1, Griffith, Kent J.1, Karty, Jonathan A.1, Mubarak, Mohammad S.2, Raghavachari, Krishnan1, Peters, Dennis G.1 peters@indiana.edu
Source: Journal of Electroanalytical Chemistry. Sep2010, Vol. 647 Issue 2, p194-203. 10p.
Subjects: Electrochemistry, Nickel catalysts, Chemical reduction, Halides, Metal complexes, Density functionals, Ring formation (Chemistry)
Abstract: Abstract: Dimethyl-, diethyl-, and diphenyl-substituted analogues of nickel(II) salen have been synthesized, and the cyclic voltammetric behavior of each compound at a glassy carbon electrode in dimethylformamide (DMF) containing tetra-n-butylammonium tetrafluoroborate (TBABF4) has been compared with that of nickel(II) salen itself. Differences in the cathodic peak potentials for these species have been rationalized with the aid of theoretical computations based on density functional theory. Cyclic voltammograms for reduction of dimethylated nickel(II) salen reveal that placing a methyl group on the carbon atom of each imino (Cf the ligand improves the performance of electrogenerated dimethylated nickel(I) salen as a catalyst for reduction of 1-iodobutane. This conclusion is supported by experiments that combine controlled-potential electrolysis with high-performance liquid chromatography–electrospray ionization–mass spectrometry (HPLC–ESI–MS) to detect and analyze the post-electrolysis nickel-containing species arising from the bulk catalytic reduction of 1-iodooctane. Additional studies have been made of the use of electrogenerated dimethylated nickel(I) salen for the catalytic reduction of alkyl halides and for the reductive intramolecular cyclization of acetylenic halides. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Electroanalytical Chemistry is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 52824087
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  Data: Electrochemistry of substituted salen complexes of nickel(II): Nickel(I)-catalyzed reduction of alkyl and acetylenic halides
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  Data: <searchLink fieldCode="AR" term="%22Foley%2C+Matthew+P%2E%22">Foley, Matthew P.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Du%2C+Peng%22">Du, Peng</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Griffith%2C+Kent+J%2E%22">Griffith, Kent J.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Karty%2C+Jonathan+A%2E%22">Karty, Jonathan A.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Mubarak%2C+Mohammad+S%2E%22">Mubarak, Mohammad S.</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Raghavachari%2C+Krishnan%22">Raghavachari, Krishnan</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Peters%2C+Dennis+G%2E%22">Peters, Dennis G.</searchLink><relatesTo>1</relatesTo><i> peters@indiana.edu</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Electroanalytical+Chemistry%22">Journal of Electroanalytical Chemistry</searchLink>. Sep2010, Vol. 647 Issue 2, p194-203. 10p.
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  Data: <searchLink fieldCode="DE" term="%22Electrochemistry%22">Electrochemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Nickel+catalysts%22">Nickel catalysts</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reduction%22">Chemical reduction</searchLink><br /><searchLink fieldCode="DE" term="%22Halides%22">Halides</searchLink><br /><searchLink fieldCode="DE" term="%22Metal+complexes%22">Metal complexes</searchLink><br /><searchLink fieldCode="DE" term="%22Density+functionals%22">Density functionals</searchLink><br /><searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink>
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  Data: Abstract: Dimethyl-, diethyl-, and diphenyl-substituted analogues of nickel(II) salen have been synthesized, and the cyclic voltammetric behavior of each compound at a glassy carbon electrode in dimethylformamide (DMF) containing tetra-n-butylammonium tetrafluoroborate (TBABF4) has been compared with that of nickel(II) salen itself. Differences in the cathodic peak potentials for these species have been rationalized with the aid of theoretical computations based on density functional theory. Cyclic voltammograms for reduction of dimethylated nickel(II) salen reveal that placing a methyl group on the carbon atom of each imino (Cf the ligand improves the performance of electrogenerated dimethylated nickel(I) salen as a catalyst for reduction of 1-iodobutane. This conclusion is supported by experiments that combine controlled-potential electrolysis with high-performance liquid chromatography–electrospray ionization–mass spectrometry (HPLC–ESI–MS) to detect and analyze the post-electrolysis nickel-containing species arising from the bulk catalytic reduction of 1-iodooctane. Additional studies have been made of the use of electrogenerated dimethylated nickel(I) salen for the catalytic reduction of alkyl halides and for the reductive intramolecular cyclization of acetylenic halides. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Journal of Electroanalytical Chemistry is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.jelechem.2010.06.001
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      – Code: eng
        Text: English
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        PageCount: 10
        StartPage: 194
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      – SubjectFull: Electrochemistry
        Type: general
      – SubjectFull: Nickel catalysts
        Type: general
      – SubjectFull: Chemical reduction
        Type: general
      – SubjectFull: Halides
        Type: general
      – SubjectFull: Metal complexes
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      – SubjectFull: Density functionals
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      – SubjectFull: Ring formation (Chemistry)
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      – TitleFull: Electrochemistry of substituted salen complexes of nickel(II): Nickel(I)-catalyzed reduction of alkyl and acetylenic halides
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              Text: Sep2010
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