New hypervalent iodine reagents for electrophilic trifluoromethylation and their precursors: synthesis, structure, and reactivity

Several new five- and a six-membered heterocyclic monochloroiodanes, including two cationic species, were synthesized. Three of which were used for the preparation of corresponding trifluoromethylation reagents. These compounds were characterized by X-ray crystallography for a comparative structural...

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Bibliographic Details
Published in:Tetrahedron 2010-07, Vol.66 (31), p.5753-5761
Main Authors: Niedermann, Katrin, Welch, Jan M., Koller, Raffael, Cvengroš, Ján, Santschi, Nico, Battaglia, Philip, Togni, Antonio
Format: Article
Language:English
Subjects:
Hypervalent iodine
Monochloroiodane
Reactivity study
Trifluoromethylation
X-ray analysis
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Summary:Several new five- and a six-membered heterocyclic monochloroiodanes, including two cationic species, were synthesized. Three of which were used for the preparation of corresponding trifluoromethylation reagents. These compounds were characterized by X-ray crystallography for a comparative structural study. A reactivity study on the trifluoromethylation of para-toluenesulfonic acid has been conducted in order to compare initial rates. Compounds having a longer I–O bond display a higher reactivity. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.04.125