Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 45, Pages 14473-14480Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b09636
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Funding
- National Science Foundation [CBET 1438493]
- NSF-MRI grant [CHE-1229030]
- Rutgers University
- Direct For Mathematical & Physical Scien [1229030] Funding Source: National Science Foundation
- Division Of Chemistry [1229030] Funding Source: National Science Foundation
- Div Of Chem, Bioeng, Env, & Transp Sys
- Directorate For Engineering [1438493] Funding Source: National Science Foundation
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Transition-metal-catalyzed alkylation reactions of arenes have become a central transformation in organic synthesis. Herein, we report the first general strategy for alkylation of arenes with styrenes and alcohols catalyzed by carbon-based materials, exploiting the unique property of graphenes to produce valuable diarylalkane products in high yields and excellent regioselectivity. The protocol is characterized by a wide substrate scope and excellent functional group tolerance. Notably, this process constitutes the first general application of graphenes to promote direct CC bond formation utilizing polar functional groups anchored on the GO surface, thus opening the door for an array of functional group alkylations using benign and readily available graphene materials. Mechanistic studies suggest that the reaction proceeds via a tandem catalysis mechanism in which both of the coupling partners are activated by interaction with the GO surface.
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