HIGES

Hypervalent Iodine Research

Goal: The goal of this project is to develop a novel reaction methodology that uses hypervalent iodine to avoid β-hydride elimination; a detrimental side reaction that plagues current Pd-catalyzed cross-coupling methods.

The Hypervalent Iodine-Guided Electrophilic Substitution (HIGES) reaction is a methodology created by the Hyatt Research group in which hypervalent iodine and benzyl metalloids are utilized to couple two carbon groups together to form para-selective benzylation products. A model hypervalent iodine system that demonstrates the propensity to form C-C bonds is the reductive iodonio-Claisen rearrangement (RICR) in which hypervalent iodine compounds are used to produce ortho-selective C-C products. The metal-like properties and hypernucleofugality of hypervalent iodine allow for the transmetallation with the metalloid reactants to result in a C-C bond formation. The formation of carbon-carbon bonds are an active research interest in the synthetic community, but many methods have problems when trying to couple two different sp³ hybridized carbon atoms. The most common difficulty encountered is the propensity of sp³ carbons to undergo β-hydride elimination thus shutting down the catalytic process and creating side-products. Future reactivity involving hypervalent iodine-guided electrophilic substitutions could potentially be a growing field in the hypervalent iodine community due to the unique properties that iodine exhibits.

Other research:

• Formation of Spirolactams for Trichomoniasis Vaginalis
• Antibiotic Dental Composites
• High Temperature Superconductivity

See related publications:

• Cyrus Mowdawalla^AU, Faiz Ahmed^AU, Tian Li^AU, Kiet Pham^AU, Loma Dave^AU, Grace Kim^AU, I. F. Dempsey Hyatt, Beilstein Journal of Organic Chemistry, 2018, 14, 1039–1045. Hypervalent iodine-guided electrophilic substitution: para-selective substitution across aryl iodonium compounds with benzyl groups
• I. F. Dempsey Hyatt, Loma Dave^AU, Navindra David^AU, Kirandeep Kaur^AU, Marly Medard^AU, Cyrus Mowdawalla^AU, Organic and Biomolecular Chemistry 2019, 17, 7822-7848. Hypervalent iodine reactions utilized in carbon-carbon bond formations
• Christina Callovi^AU, Su Wint War^AU, Calvin N. Semczuk^AU, Madison Fisher^AU, Matthew Lucero Rodriguez^AU, Joshua Plaut^AU, Ivana Joshi^AU, I. F. Dempsey Hyatt and Daniel L. Silverio, ARKIVOC, 2022, 126-137. Synthesis and properties of liquid phenyliodine dicarboxylates