Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 5, Pages 1876-1880Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510180
Keywords
alkenes; allylic compounds; copper; isomerization; N-heterocyclic carbenes
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Funding
- Institute for Basic Science in Korea [IBS-R010-D1]
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New reactivity of a [Cu(NHC)] (NHC = N-heterocyclic carbene) catalyst is disclosed for the efficient C-H allylation of polyfluoroarenes using allyl halides in benzene at room temperature. The same catalyst system also promotes an isomerization-induced alkenylation of initially the generated allyl arenes when the reaction is run in tetrahydrofuran. Significantly, not only electron-deficient but also electron-rich (hetero)arenes undergo this double-bond migration process, thus leading to alkenylated products. The present system features mild reaction conditions, broad scope with respect to the arene substrates and allyl halide reactants, good functional-group tolerance, and high stereoselectivity.
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