Investigations from our group have resulted in a series of stable and soluble IBX analogs: IBX–amides, IBX–esters and NIPAs. These readily available hypervalent iodine reagents possess reactivity similar to IBX and DMP, and proved to be useful oxidizing reagents towards alcohols and sulfides. The synthesis of polymer supported NIPAs has been reported as well.
Our research program in general is aimed at the development of new synthetic methodologies based on the organic chemistry of hypervalent main–group elements. Hypervalent compounds are generally defined as "ions or molecules of the elements of Groups 15–18 bearing more electrons than the octet within a valence shell." In current synthetic literature, this terminology is commonly applied toward the synthetically useful organic reagents, derivatives of main–group elements in high oxidation states, such as polyvalent iodine, tellurium, selenium, antimony, and bismuth. It has been recognized that there are many similarities between hypervalent main–group compounds and organic transition metal complexes. The reactions of hypervalent molecules are commonly discussed in terms of oxidative addition, reductive elimination, ligand exchange, and ligand coupling, which are typical of the transition metal chemistry. Exploration and practical utilization of these similarities may lead to the development of new useful methodologies for modern organic synthesis.
Specific objectives of our current research program include: (1) the development of new synthetic methodologies based on hypervalent iodine compounds, (2) the preparation, structural characterization, and synthetic utilization of new hypervalent iodine heterocycles and mixed phosphonium–iodonium ylides, (3) the preparation, structural study and exploration of the chemistry of hitherto unknown complexes of hypervalent xenon and novel organobismuth(V) cyclic derivatives. Our recent achievements include the preparation and synthetic utilization of new phosphoranyl–derived iodanes (Scheme 1), the synthesis of new complexes of polyvalent iodine with nitrogen ligands (Scheme 2), preparation and structural investigation of new amino acid–based benziodazoles (Scheme 3), and the development of new synthetically useful oxidizing reagents (Scheme 4).