Iodosobenzene tetrafluoroborate: First example of a stable electrophilic hypervalent iodine reagent without nucleophilic ligands

✍ Scribed by Viktor V. Zhdankin; Rik Tykwinski; Ronald Caple; Bruce Berglund; Anatoly S. Koz'min; Nikolai S. Zefirov

• Book ID: 104217604
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 204 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82162-0

✦ Synopsis

Iodosobenzene tetrafluoroborate 1 has been prepared by the reaction of PhI(OAo)p and aqueous BRF4, and its reactions with alkenes, sllyl enol ethers, and aoetylenes have been studied. A considerable number of hypervalent Iodine reagents have been developed in the last oentury, and many of these have found wide synthetic applications [la]. Most of these reagents are derivatives of carboxylio or strong inorganic acids Cl], anions of which oan partioipate in reactions as nuoleophlles. Until now only two examples of eleatrophillc iodine reagents without nucleophllio anionic ligands were known: oomplexes of PhIO with RF3 [2al and Bt30+PPq' [2b], which are unstable even at O°C. In this artlole we report the synthesis of the first stable hypervalent Iodine reagent without a nucleophllio ligandlodosobenzene tetrafluoroborate 1. Compound 1 Is easily prepared by the reaction of commerolally available iodosobenzene dlacetate and aqueous RBF4, yielding a yellow, crystalline product with mp l6OoC c31.