Journal
ACS CATALYSIS
Volume 2, Issue 4, Pages 521-527Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs300089y
Keywords
methyltrioxorhenium; electrophilic trifluoromethylation; catalytic trifluoromethylation; hypervalent iodine; radical reactions
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Funding
- ETH Zurich
- Schweizerische Nationalfonds (SNF)
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Methyltrioxorhenium acts as a catalyst (5-10 Mol %) for the direct electrophilic trifluoromethylation of various aromatic and heteroaromatic compounds using the hypervalent iodine reagent 1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one (1). The products are formed in up to 77% yield. Mixtures of regioisomers are obtained in the case of substituted and heteroaromatic substrates. The reaction, typically carried out in chloroform solvent at 70 degrees C, shows a significant induction period. Monitoring by EPR shows the involvement of radical species. A small kinetic deuterium isotope effect of 1.3 is observed for benzene.
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