MAu2GeS4-Chalcogel (M = Co, Ni): Heterogeneous Intra- and Intermolecular Hydroamination Catalysts

Bambar Davaasuren; Abdul-Hamid M. Emwas; Alexander Rothenberger

doi:10.1021/acs.inorgchem.7b01099

MAu2GeS4-Chalcogel (M = Co, Ni): Heterogeneous Intra- and Intermolecular Hydroamination Catalysts

Bambar Davaasuren, Abdul-Hamid M. Emwas, Alexander Rothenberger

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

High surface area macroporous chalcogenide aerogels (chalcogels) MAu2GeS4 (M = Co, Ni) were prepared from K2Au2GeS4 precursor and Co(OAc)2 or NiCl2 by one-pot sol-gel metathesis reactions in aqueous media. The MAu2GeS4-chalcogels were screened for catalytic intramolecular hydroamination of 4-pentyn-1-amine substrate at different temperatures. 87% and 58% conversion was achieved at 100 °C, using CoAu2GeS4- and NiAu2GeS4-chalcogels respectively, and the reaction kinetics follows the first order. It was established that the catalytic performance of the aerogels is associated with the M(2+) centers present in the structure. Intermolecular hydroamination of aniline with 1-R-4-ethynylbenzene (R = -H, -OCH3, -Br, -F) was carried out at 100 °C using CoAu2GeS4-chalcogel catalyst, due to its promising catalytic performance. The CoAu2GeS4-chalcogel regioselectively converted the pair of substrates to respective Markovnikov products, (E)-1-(4-R-phenyl)-N-phenylethan-1-imine, with 38% to 60% conversion.

Original language	English (US)
Pages (from-to)	9609-9616
Number of pages	8
Journal	Inorganic Chemistry
Volume	56
Issue number	16
DOIs	https://doi.org/10.1021/acs.inorgchem.7b01099
State	Published - Aug 8 2017

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This research was supported by King Abdullah University of Science and Technology (KAUST) baseline funding. We would like to thank Prof. P. W. Roesky for the advice in catalytic activity measurement and Dr. E. Ahmed for the assistance in chalcogel preparation.

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10.1021/acs.inorgchem.7b01099

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title = "MAu2GeS4-Chalcogel (M = Co, Ni): Heterogeneous Intra- and Intermolecular Hydroamination Catalysts",

abstract = "High surface area macroporous chalcogenide aerogels (chalcogels) MAu2GeS4 (M = Co, Ni) were prepared from K2Au2GeS4 precursor and Co(OAc)2 or NiCl2 by one-pot sol-gel metathesis reactions in aqueous media. The MAu2GeS4-chalcogels were screened for catalytic intramolecular hydroamination of 4-pentyn-1-amine substrate at different temperatures. 87% and 58% conversion was achieved at 100 °C, using CoAu2GeS4- and NiAu2GeS4-chalcogels respectively, and the reaction kinetics follows the first order. It was established that the catalytic performance of the aerogels is associated with the M(2+) centers present in the structure. Intermolecular hydroamination of aniline with 1-R-4-ethynylbenzene (R = -H, -OCH3, -Br, -F) was carried out at 100 °C using CoAu2GeS4-chalcogel catalyst, due to its promising catalytic performance. The CoAu2GeS4-chalcogel regioselectively converted the pair of substrates to respective Markovnikov products, (E)-1-(4-R-phenyl)-N-phenylethan-1-imine, with 38% to 60% conversion.",

author = "Bambar Davaasuren and Emwas, {Abdul-Hamid M.} and Alexander Rothenberger",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This research was supported by King Abdullah University of Science and Technology (KAUST) baseline funding. We would like to thank Prof. P. W. Roesky for the advice in catalytic activity measurement and Dr. E. Ahmed for the assistance in chalcogel preparation.",

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AU - Davaasuren, Bambar

AU - Emwas, Abdul-Hamid M.

AU - Rothenberger, Alexander

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This research was supported by King Abdullah University of Science and Technology (KAUST) baseline funding. We would like to thank Prof. P. W. Roesky for the advice in catalytic activity measurement and Dr. E. Ahmed for the assistance in chalcogel preparation.

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AB - High surface area macroporous chalcogenide aerogels (chalcogels) MAu2GeS4 (M = Co, Ni) were prepared from K2Au2GeS4 precursor and Co(OAc)2 or NiCl2 by one-pot sol-gel metathesis reactions in aqueous media. The MAu2GeS4-chalcogels were screened for catalytic intramolecular hydroamination of 4-pentyn-1-amine substrate at different temperatures. 87% and 58% conversion was achieved at 100 °C, using CoAu2GeS4- and NiAu2GeS4-chalcogels respectively, and the reaction kinetics follows the first order. It was established that the catalytic performance of the aerogels is associated with the M(2+) centers present in the structure. Intermolecular hydroamination of aniline with 1-R-4-ethynylbenzene (R = -H, -OCH3, -Br, -F) was carried out at 100 °C using CoAu2GeS4-chalcogel catalyst, due to its promising catalytic performance. The CoAu2GeS4-chalcogel regioselectively converted the pair of substrates to respective Markovnikov products, (E)-1-(4-R-phenyl)-N-phenylethan-1-imine, with 38% to 60% conversion.

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ER -

MAu2GeS4-Chalcogel (M = Co, Ni): Heterogeneous Intra- and Intermolecular Hydroamination Catalysts

Abstract

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CCDC 1546598: Experimental Crystal Structure Determination

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MAu2GeS4-Chalcogel (M = Co, Ni): Heterogeneous Intra- and Intermolecular Hydroamination Catalysts

Abstract

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CCDC 1546598: Experimental Crystal Structure Determination

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