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Novel 10‐I‐3 Hypervalent Iodine‐Based Compounds for Electrophilic Trifluoromethylation
Author(s) -
Eisenberger Patrick,
Gischig Sebastian,
Togni Antonio
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501052
Subject(s) - hypervalent molecule , trifluoromethylation , electrophile , umpolung , chemistry , nucleophile , trifluoromethyl , moiety , reactivity (psychology) , iodine , medicinal chemistry , ligand (biochemistry) , nucleophilic substitution , organic chemistry , combinatorial chemistry , alkyl , catalysis , medicine , biochemistry , alternative medicine , receptor , pathology
The synthesis of a new family of 10‐I‐3 hypervalent iodine compounds is described in which the CF 3 functionality participates directly in the hypervalent bond. These materials are accessible by nucleophilic ligand substitution at iodine using Me 3 SiCF 3 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‐(1 H )‐one and two substituted 1‐trifluoromethyl‐1,3‐dihydro‐1,2‐benziodoxoles). Preliminary results for the direct electrophilic transfer of the trifluoromethyl 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 CF 3 group.