Enhancing the solubility for hypervalent ortho-sulfonyl iodine compounds

The synthesis and characterization of new hypervalent iodine reagents ArINTs (2a), ArIO (3a), and ArIO₂ (4a) (Ar=2-tert-butylsulfonyl-5-tert-butylphenyl) are described. These reagents are compared to previously reported analogous set of reagents Ar=2-tert-butylsulfonylphenyl and found to have significantly enhanced solubility and similar chemical reactivity. The X-ray crystal structures of 4a and of ArI (1a) (Ar=2-tert-butylsulfonyl-5-tert-butylphenyl) are discussed and compared. These reagents find use in atom and group transfer reactions.