1-(Trifluoromethyl)-1,2-benziodoxol-3(1<i>H</i>)-one

Stanek, Kyrill; Koller, Raffael; Kieltsch, Iris; Eisenberger, Patrick; Togni, Antonio

doi:10.1002/047084289x.rn01121

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“…In 2006, our group developed a new class of electrophilic trifluoromethylating reagents based on hypervalent iodine, including 1-(trifluoromethyl)-1,2-benziodoxol-3(1 H )-one ( 1 ) and trifluoromethyl-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole ( 2 ), , both easily accessible in high yields from o -iodobenzoic acid, and commercially available CF 3 TMS (Ruppert–Prakash reagent). , Reagents 1 and 2 have been used successfully in our laboratories for the direct electrophilic trifluoromethylation of β-keto esters, sulfur centered nucleophiles, α-nitro esters, phosphines, phenolates, and alcohols and for the Ritter-type N-trifluoromethylation of nitriles (Scheme ). Finally, several other research groups have used reagents 1 or 2 for the trifluoromethylation of a variety of substrates. − …”

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confidence: 99%

Rhenium-Catalyzed Trifluoromethylation of Arenes and Heteroarenes by Hypervalent Iodine Reagents

2012

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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 °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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