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.
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