Research in Hypervalent Iodine Chemistry
Most people are familiar with the element iodine due to its popularity as an antiseptic sold as iodine tinctures. These alcohol containing solutions cause iodine to have a brown color through the generation of something called a charge transfer complex. If iodine is not in an alcohol solution, if forms a different charge transfer complex with air that makes it take on a purple color. However, when in a vacuum, iodine looks like a silvery metal (see pictures on the right). Iodine is an immensely diverse element and exploring the metal-like properties of compounds containing iodine in its hypervalent state is the main focus of the Hyatt Research Group.
When chemists call something "hypervalent" it means that the normal rules of bonding do not apply. Typically, nonmetals follow the octet rule; they prefer to form structures with eight shared electrons around each element. Hypervalency is when compounds form with over eight electrons. In our group, we use iodine(III) which has 10 electrons in most structures. In this higher oxidation state, the hypervalency can be used to exploit unusual and often unexplored metal-like properties of this commonly encountered nonmetal.
Cyrus Mowdawalla, Faiz Ahmed, Tian Li, Kiet Pham, Loma Dave, Grace Kim, I. F. Dempsey Hyatt, Beilstein Journal of Organic Chemistry 2018 accepted. Hypervalent Iodine-Guided Electrophilic Substitution: Hypervalent iodine-guided electrophilic substitution: para-selective substitution across aryl iodonium compounds with benzyl groups
Hypervalent Iodonium Alkynyl Triflates (HIAT) are used to generate a trimethylenemethane (TMM) intermediate the can quickly add molecular complexity towards a targeted synthesisLearn more
Aggregation Induced Emission of Cycloheptatrienylidenes
Hypervalent Iodonium Alkynyl Triflates (HIAT) undergo a ring-expansion reaction with a benzene ring to synthesize cycloheptatrienylidene (CHT). The molecule is then treated with a metal ion to initiate a aggregation that induces fluorescence.Learn more
Formation and Decomposition Products of Alkylated Hypervalent Iodine
Alkyl trifluoroborates are used in a transmetallation reaction with hypervalent iodine to create a highly reactive alkylated hypervalent iodine intermediate. Different reactants can then be added to form various products in this new reaction methodology.Learn more