期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 12, 期 9, 页码 2579-2586出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200501052
关键词
hypervalent compounds; iodine; trifluoromethylation; umpolung
The synthesis of a new family of 10-1-3 hypervalent iodine compounds is described in which the CF3 functionality participates directly in the hypervalent bond. These materials are accessible by nucleophilic ligand substitution at iodine using Me3SiCF3 in the presence of a substoichiometric amount of fluoride. The expected T-shaped geometry at iodine was verified by X-ray crystallographic analyses of three of the products (1-trifluoromethyl-1,2-benziodoxol-3-(H)-one and two Substituted l-trifluoromethyl-.1,3-dihydro-1,2-benziodoxoles). Preliminary results for the direct electrophilic transfer of the trifluorormethyl moiety onto organic nucleophiles show modest reactivity in polar aprotic solvents under relatively mild conditions. The overall process can be understood as a formal umpolung of the CF3 group.
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