Aspects of the Chemical Energetics of the Hypervalent Benzene‐Based Organohalogen Halosyl, Halyl, and Perhalyl Species

Ponikvar‐Svet, Maja; Liebman, Joel F.

doi:10.1002/9780470682531.pat0940

Patai's Chemistry of Functional Groups 2018

DOI: 10.1002/9780470682531.pat0940

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Aspects of the Chemical Energetics of the Hypervalent Benzene‐Based Organohalogen Halosyl, Halyl, and Perhalyl Species

Maja Ponikvar‐Svet

Joel F. Liebman

Abstract: In this chapter, we discuss the chemical energetics of the hypervalent benzene‐based organohalogen halosyl, halyl, and perhalyl species in its broadest sense. Our discussion includes calorimetric measurements, ionization potentials, equilibrium constants, and electrochemical quantities such as redox potentials.

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Cited by 3 publications

References 125 publications

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Electrocatalytic Synthesis of Substituted Pyrazoles via Hypervalent Iodine Mediated Intramolecular C−N Coupling

et al. 2022

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The electrochemical intramolecular cross‐dehydrogenative C(sp2)−H/N−H coupling of α,β‐unsaturated hydrazones resulting in substituted pyrazoles has been discovered. The process is catalyzed by hypervalent iodine species generated in situ through anodic oxidation of aryl iodide in fluorinated alcohol media. The formation of hypervalent iodine compound and its key role in the construction of a new C−N bond was confirmed with CV and NMR experiments. A wide range of substituted pyrazoles were obtained in yields ranging from 46% to 88%.

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Electrocatalytic Synthesis of Substituted Pyrazoles via Hypervalent Iodine Mediated Intramolecular C−N Coupling

et al. 2022

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Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization**

Liu

Heinis

et al. 2023

Angewandte Chemie

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Herein, we report a novel strategy for the modification of peptides based on the introduction of highly reactive hypervalent iodine reagents-ethynylbenziodoxolones (EBXs)-onto peptides. These peptide-EBXs can be readily accessed, by both solutionand solid-phase peptide synthesis (SPPS). They can be used to couple the peptide to other peptides or a protein through reaction with Cys, leading to thioalkynes in organic solvents and hypervalent iodine adducts in water buffer. Furthermore, a photocatalytic decarboxylative coupling to the C-terminus of peptides was developed using an organic dye and was also successful in an intramolecular fashion, leading to macrocyclic peptides with unprecedented crosslinking. A rigid linear aryl alkyne linker was essential to achieve high affinity for Keap1 at the Nrf2 binding site with potential proteinprotein interaction inhibition.

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Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization**

Liu

Heinis

et al. 2023

Angew Chem Int Ed

View full text Add to dashboard Cite

Herein, we report a novel strategy for the modification of peptides based on the introduction of highly reactive hypervalent iodine reagents—ethynylbenziodoxolones (EBXs)—onto peptides. These peptide‐EBXs can be readily accessed, by both solution‐ and solid‐phase peptide synthesis (SPPS). They can be used to couple the peptide to other peptides or a protein through reaction with Cys, leading to thioalkynes in organic solvents and hypervalent iodine adducts in water buffer. Furthermore, a photocatalytic decarboxylative coupling to the C‐terminus of peptides was developed using an organic dye and was also successful in an intramolecular fashion, leading to macrocyclic peptides with unprecedented crosslinking. A rigid linear aryl alkyne linker was essential to achieve high affinity for Keap1 at the Nrf2 binding site with potential protein‐protein interaction inhibition.

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Aspects of the Chemical Energetics of the Hypervalent Benzene‐Based Organohalogen Halosyl, Halyl, and Perhalyl Species

Cited by 3 publications

References 125 publications

Electrocatalytic Synthesis of Substituted Pyrazoles via Hypervalent Iodine Mediated Intramolecular C−N Coupling

Electrocatalytic Synthesis of Substituted Pyrazoles via Hypervalent Iodine Mediated Intramolecular C−N Coupling

Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization**

Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization**

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