Organic Letters
Letter
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In summary, we developed a novel copper-catalyzed
trifluoromethylalkynylation of aliphatic isocyanides with aryla-
cetylenic triflones to generate (E)-N-alkyl trifluoromethyl
alkynyl ketoimines under mild conditions. This is a new type
of isocyanide-involved difunctionalization incorporation of
trifluoromethylation. The resulting ketoimine products are
versatile building blocks easily convertible to trifluoromethyl-
substituted N-heterocycles, propargylamines, etc. Mechanistic
studies reveals that isocyanide is not only a reactant in this
transformation but also responsible for the initial trifluoromethyl
radical formation under the aid of Cu(OAc)2.
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ASSOCIATED CONTENT
* Supporting Information
■
S
Experimental procedures and characterization data for products.
This material is available free of charge via the Internet at http://
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AUTHOR INFORMATION
Corresponding Authors
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(12) (a) Zhang, B.; Muck-Lichtenfeld, C.; Daniliuc, C. G.; Studer, A.
Angew. Chem., Int. Ed. 2013, 52, 10792. (b) Wang, Q.; Dong, X.; Xiao,
T.; Zhou, L. Org. Lett. 2013, 15, 4846. (c) Cheng, Y.; Jiang, H.; Zhang,
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Kadi, A. A.; Fun, H.-K.; Zhang, Y.; Yu, S. Synthesis 2014, 46, 2711.
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N. A.; Bacheler, L. T.; Diamond, S.; Jeffrey, S.; Klabe, R. M.; Cordova, B.
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We are grateful for financial support of this work by the National
Science Foundation of China (21202168, 21472190).
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