Electrophilic trifluoromethylation of arenes and N-heteroarenes using hypervalent iodine reagents |
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Authors: | Matthias S. Wiehn |
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Affiliation: | Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Wolfgang-Pauli-Strasse 10, ETH Zurich, 8093 Zurich, Switzerland |
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Abstract: | The reaction of hypervalent iodine trifluoromethylating reagents with a variety of arenes and N-heteroarenes gives access to the corresponding trifluoromethylated compounds. In comparative studies, 1-trifluoromethyl-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (2) proved to be the superior to 1-trifluoromethyl-1,2-benziodoxol-3-(1H)-one (1) for the direct aromatic trifluoromethylation. Depending on the individual substrates, additives such as zinc bis(trifluoromethylsulfonyl)imide or tris(trimethylsilyl)silyl chloride proved helpful in promoting the reactions. In the case of nitrogen heterocycles a pronounced tendency for the incorporation of the trifluoromethyl group at the position adjacent to nitrogen was observed. |
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Keywords: | Electrophilic trifluoromethylation Hypervalent iodine Aromatic trifluoromethylation Hypersilyl chloride |
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