Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 131, Issue 9, Pages 951-957Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2010.06.020
Keywords
Electrophilic trifluoromethylation; Hypervalent iodine; Aromatic trifluoromethylation; Hypersilyl chloride
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Funding
- ETH Zurich
- Aitor Moreno
- Karlsruhe House of Young Scientists (KHYS)
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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-((1)H)-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. (C) 2010 Elsevier B.V. All rights reserved.
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