Preparation of [hydroxy(((+)-10-camphorsulfonyl)oxy)iodo]benzene and its reactivity toward carbonyl compounds

α‐Arylation by Rearrangement: On the Reaction of Enolates with Diaryliodonium Salts

“…Camphorsulfonate was used as the chiral anion to direct the electrophile to one face of enolate 1 (Scheme 2 a). [20] The chosen PTC* + should block one face of enolate 2 as demonstrated in asymmetric S N Ar reactions of 2 (Scheme 2 b). [21] Both approaches were expected to deliver the enantiomerically enriched iodane intermediate 3, which would yield product 4 upon reductive elimination (i.e., [1,2] rearrangement).…”

Cyclopropanation of alkenes using hypervalent iodine reagents

“…As the electrophilic activation of double bond with (diacetoxyiodo)benzene is known for a long time, we tried to directly introduce the bisnucleophile thus performing the cyclopropanation in one step starting from the corresponding alkene. 8 We were pleased to find an even higher yields in the corresponding 1,1-dicyanocyclopropane derivatives of type 10. …”

α-Functionalization of Carbonyl Compounds Using Hypervalent Iodine Reagents

“…[18] In 1990 Varvoglis et al successfully prepared [hydroxy((+)-10-camphorsulfonyloxy)iodo]benzene and used this reagent in the α-(10-camphorsulfonyl)oxylation of a range of substrates including ketones, β-dicarbonyls and other carbonyls bearing an activated methylene group (Scheme 2). [19] O Over the years there have been many developments and modifications of the reaction, such as solvent-free α-sulfonyloxylation of ketones by grinding HTIB with a ketone using a pestle and mortar, [20] and use of ultrasound. [21] Nabana and Togo investigated the use of a range of [hydroxy(tosyloxy)iodo]arenes and [hydroxy(phosphoryloxy)iodo]arenes in the α-tosyloxylation and α-phosphoryloxylation of ketones respectively (Scheme 3).…”