Journal
ORGANIC LETTERS
Volume 17, Issue 9, Pages 2174-2177Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00775
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Funding
- 973 Program [2011CB808600, 2012CB725302]
- National Natural Science Foundation of China [21390400, 21025206, 21272180, 21302148]
- Research Fund for the Doctoral Program of Higher Education of China [20120141130002]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT1030]
- Chemical Sciences and Engineering Division, Argonne National Laboratory
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-AC02-06CH11357]
- Department of Energy
- MRCAT member institutions
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A novel oxidative C-H/C-H cross-coupling reaction between electron-rich arenes and alkenes is established utilizing FeCl3 as the catalyst and DDQ as the oxidant. Interestingly, direct arylation products are obtained with diaryl-ethylenes and double arylation products are obtained with styrene derivatives, which show high chemoselectivity and good substrate scope. A radical trapping experiment and EPR (electron paramagnetic resonance) experiments indicate that this reaction proceeds through a radical pathway in which DDQ plays a key role in the aryl radical formation. XAFS (X-ray absorption fine structure) experiments reveal that the oxidation state of the iron catalyst does not change during the reaction, suggesting that FeCl3 might be used as a Lewis acid. Finally, a detailed mechanism is proposed for this transformation.
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