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Hypervalent Iodine-Guided Electrophilic Substitution

  • 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.
  • Summary: 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.