Journal
JOURNAL OF CATALYSIS
Volume 315, Issue -, Pages 41-47Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.jcat.2014.04.004
Keywords
Gold catalysis; Supported gold nanoparticles; C-C bond formation; Waste-free formation of biaryls; Activation of non-activated arenes
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Funding
- Project CONSOLIDER INGENIO (MULTICAT)
- SEVERO OCHOA Program for centers of excellence
- European Union Seventh Framework Programme [PIOF-GA-2009-253129]
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Small gold nanoparticles in the presence of O-2 are able to cleave C-H bonds of non-activated arenes and facilitate catalytic formation of biaryls under mild conditions. This procedure avoids the common requirement of iodine, acids, bases, and/or other stoichiometrical additives to accomplish multiple turnovers and results in a zero-waste synthetic process. A number of unactivated arenes such as benzene, toluene, p-xylene, nitrobenzene, chlorobenzene, or phenol are selectively converted to the corresponding biaryls, with accumulated turnover numbers greater than 600. Kinetic measurements, in combination with IR, HRTEM, and STEM-HAADF data, suggest that the reaction takes place on gold atoms that are metallic in character, with the highest C-C bond formation rate provided by gold nanoparticles of approximately 3 nm of diameter. A radical-free reaction mechanism is postulated on the basis of the kinetic measurements. The results represent a first stone for the waste-free preparation of biaryls using supported gold catalysts. (C) 2014 Elsevier Inc. All rights reserved.
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