Synthesis of Hypervalent Iodine(III) Pseudocyclic Iodoarene Derivatives Stabilized by Internal Halogen Bonding

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Synthesis of Hypervalent Iodine(III) Pseudocyclic Iodoarene Derivatives Stabilized by Internal Halogen Bonding

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Tyson, Daniel R

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2024-04-18

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Abstract

Hypervalent iodine compounds can serve as highly efficient electrophilic group transfer reagents (Talavera et al., 2015). This unique property, as well as the wide commercial availability and low environmental impact of iodine, has led to increased use of hypervalent iodine reagents in many common synthetic pathways, including trifluoromethylation, arylation, amination, and halogenation (Talavera et al., 2015). Furthermore, halogen bonding has been widely used in the structural chemistry of hypervalent iodine compounds to improve stability, solubility, and reactivity (Li et al., 2022). Here, several ortho halogen substituted pseudocyclic [(hydroxy)tosyloxy]iodoarenes, stabilized by internal halogen bonding, have been synthesized as ideal precursors in the preparation of hypervalent iodine electrophilic group transfer reagents. Furthermore, their use in the preparation of electrophilic group transfer reagents is believed to have been demonstrated by the synthesis of a novel pyrrolidine derivative. Such pseudocyclic reagents are stabilized by internal halogen bonding, potentially affording a wider variety of applications in comparison to analogous unsubstituted reagents. In the future, this research can be furthered by the synthesis of other pseudocyclic pyrrole iodoarenes by reactions of these [(hydroxy)tosyloxy]iodoarenes with various pyrrole derivatives (as shown below). Long term, this project can be continued by the synthesis of pseudocyclic iodoarenes of other nucleophiles, such as trifluoromethane, halogens, and amines.

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University Honors

University of Minnesota Duluth

Department of Chemistry and Biochemistry

Swenson College of Science and Engineering

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This item is a University Honors Capstone.

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Tyson, Daniel R. (2024). Synthesis of Hypervalent Iodine(III) Pseudocyclic Iodoarene Derivatives Stabilized by Internal Halogen Bonding. Retrieved from the University Digital Conservancy, https://hdl.handle.net/11299/262453.

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