Atom-economical group-transfer reactions with hypervalent iodine compounds.
TLDR
A brief summary of recently developed methods, in which this arising former waste is used as an additional reagent in cascade transformations to generate multiple substituted products in one step and with high atom efficiency.Abstract:
Hypervalent iodine compounds, in particular aryl-λ3-iodanes, have been used extensively as electrophilic group-transfer reagents. Even though these compounds are superior substrates in terms of reactivity and stability, their utilization is accompanied by stoichiometric amounts of an aryl iodide as waste. This highly nonpolar side product can be tedious to separate from the desired target molecules and significantly reduces the overall atom efficiency of these transformations. In this short review, we want to give a brief summary of recently developed methods, in which this arising former waste is used as an additional reagent in cascade transformations to generate multiple substituted products in one step and with high atom efficiency.read more
Citations
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A bidentate iodine(III)‐based halogen‐bond donor as a powerful organocatalyst
TL;DR: The first application of a bidentate bis(iodolium) salt as organocatalyst in a Michael and a nitro‐Michael addition reaction as well as in a Diels–Alder reaction that had not been activated by noncovalent organoc atalysts before.
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A Triazole-Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations.
TL;DR: The main advantage of this triazole‐substituted chiral aryl iodide is the excellent performance in a plethora of mechanistically diverse enantioselective transformations, such as spirocyclizations, phenol dearomatizations, α‐oxygenations, and oxidative rearrangements.
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Hypervalent Iodine(III) Compounds as Biaxial Halogen Bond Donors
TL;DR: This work presents the first systematic investigation on biaxial binding to such Lewis acids in solution through 1H NMR spectroscopy and isothermal titration calorimetry on iodine(III) derivatives.
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Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years.
TL;DR: This review outlines the main advances in the past 10 years in regard to alkene heterofunctionalization chemistry using achiral and chiral hypervalent iodine reagents and catalysts.
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N-Heterocycle-Stabilized Iodanes: From Structure to Reactivity.
TL;DR: This work presents the first systematic investigation of pseudocyclic N-heterocycle-stabilized iodanes (NHIs) and reports on their reactivity, which is highly tunable, depending on the stabilizing heterocycle.
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