Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 34, Pages 10848-10853Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802548
Keywords
C-C coupling; graphene oxide; metal-free catalysis; zigzag edges
Categories
Funding
- NNSFC [51502174]
- Shenzhen Peacock Plan [KQJSCX20170727100802505, KQTD2016053112042971]
- National Research Foundation, Singapore [NRF-NRF12015-01]
- Educational Commission of Guangdong Province [2016KCXTD006, 2016KSTCX126]
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The development of graphene oxide (GO)-based materials for C-C cross-coupling represents a significant advance in carbocatalysis. Although GO has been used widely in various catalytic reactions, the scope of reactions reported is quite narrow, and the relationships between the type of functional groups present and the specific activity of the GO are not well understood. Herein, we explore CH-CH-type cross-coupling of xanthenes with arenes using GO as real carbocatalysts, and not as stoichiometric reactants. Mechanistic studies involving molecular analogues, as well as trapped intermediates, were carried out to probe the active sites, which were traced to quinone-type functionalities as well as the zigzag edges in GO materials. GO-catalyzed cross-dehydrogenative coupling is operationally simple, shows reusability over multiple cycles, can be conducted in air, and exhibits good functional group tolerance.
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