Functionalization of Hydrogenated Graphene: Transition-Metal-Catalyzed Cross-Coupling Reactions of Allylic C−H Bonds

Chun Kiang Chua; Zdeněk Sofer; Martin Pumera

doi:10.1002/anie.201605457

Functionalization of Hydrogenated Graphene: Transition-Metal-Catalyzed Cross-Coupling Reactions of Allylic C−H Bonds

Chun Kiang Chua, Zdeněk Sofer, Martin Pumera

Department of Chemical and Biomolecular Engineering

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

17 Citations (Scopus)

Abstract

The chemical functionalization of hydrogenated graphene can modify its physical properties and lead to better processability. Herein, we describe the chemical functionalization of hydrogenated graphene through a dehydrogenative cross-coupling reaction between an allylic C−H bond and the α-C−H bond of tetrahydrothiophen-3-one using Cu(OTf)₂as the catalyst and DDQ as the oxidant. The chemical functionalization was confirmed by X-ray photoelectron spectroscopy and Fourier transform infrared spectroscopy and visualized by scanning electron microscopy. The functionalized hydrogenated graphene material demonstrated improved dispersion stability in water, bringing new quality to the elusive hydrogenated graphene (graphane) materials. Hydrogenated graphene provides broad possibilities for chemical modifications owing to its reactivity.

Original language	English
Pages (from-to)	10751-10754
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	36
DOIs	https://doi.org/10.1002/anie.201605457
Publication status	Published - 2016 Aug 26

Bibliographical note

Funding Information:
This work was supported by a Tier 2 grant (MOE2013-T2-1-056; ARC 35/13) from the Ministry of Education, Singapore. Z.S. was supported by the Czech Science Fundation (GACR No. 15-09001S).

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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title = "Functionalization of Hydrogenated Graphene: Transition-Metal-Catalyzed Cross-Coupling Reactions of Allylic C−H Bonds",

abstract = "The chemical functionalization of hydrogenated graphene can modify its physical properties and lead to better processability. Herein, we describe the chemical functionalization of hydrogenated graphene through a dehydrogenative cross-coupling reaction between an allylic C−H bond and the α-C−H bond of tetrahydrothiophen-3-one using Cu(OTf)2as the catalyst and DDQ as the oxidant. The chemical functionalization was confirmed by X-ray photoelectron spectroscopy and Fourier transform infrared spectroscopy and visualized by scanning electron microscopy. The functionalized hydrogenated graphene material demonstrated improved dispersion stability in water, bringing new quality to the elusive hydrogenated graphene (graphane) materials. Hydrogenated graphene provides broad possibilities for chemical modifications owing to its reactivity.",

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AU - Pumera, Martin

N1 - Funding Information: This work was supported by a Tier 2 grant (MOE2013-T2-1-056; ARC 35/13) from the Ministry of Education, Singapore. Z.S. was supported by the Czech Science Fundation (GACR No. 15-09001S). Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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AB - The chemical functionalization of hydrogenated graphene can modify its physical properties and lead to better processability. Herein, we describe the chemical functionalization of hydrogenated graphene through a dehydrogenative cross-coupling reaction between an allylic C−H bond and the α-C−H bond of tetrahydrothiophen-3-one using Cu(OTf)2as the catalyst and DDQ as the oxidant. The chemical functionalization was confirmed by X-ray photoelectron spectroscopy and Fourier transform infrared spectroscopy and visualized by scanning electron microscopy. The functionalized hydrogenated graphene material demonstrated improved dispersion stability in water, bringing new quality to the elusive hydrogenated graphene (graphane) materials. Hydrogenated graphene provides broad possibilities for chemical modifications owing to its reactivity.

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Functionalization of Hydrogenated Graphene: Transition-Metal-Catalyzed Cross-Coupling Reactions of Allylic C−H Bonds

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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