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Dr. Hiromichi Egami, Ryo Shimizu, Shintaro Kawamura and Prof. Dr. Mikiko Sodeoka Alkene Trifluoromethylation Coupled with C[BOND]C Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles Angewandte Chemie International Edition 52

Article first published online: 26 FEB 2013 | DOI: 10.1002/anie.201210250

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The combo pack: Copper-catalyzed trifluoromethylation of alkenes bearing an allylic proton combined with C[BOND]C bond formation affords the title compounds in good to high yields (see scheme). The reactions are faster than allylic trifluoromethylation, especially in 1,4-dioxane. A unique 1,6-oxytrifluoromethylation occurred instead of an anticipated seven-membered ring forming carbotrifluoromethylation reaction.

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