2023
DOI: 10.1002/ejoc.202201156
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Iodine and Iodide in Reductive Transformations

Abstract: This review provides a comprehensive overview of strategies and methodologies for reducing CÀ O and heteroatomicÀ oxygen bonds (NÀ O, SÀ O, PÀ O) using I 2 /I À , as well as other synthetically relevant bonds such as CÀ C, NÀ N, CÀ N, CÀ X, CÀ S. It highlights and discusses most of the mechanistic details provided by the original authors. Selected examples of other halides (Br and Cl) as reductants are also covered.

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Cited by 13 publications
(7 citation statements)
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“…The phenomenon of I 2 forming covalent bonds with unsaturated hydrocarbon compounds is a well-established concept and has been extensively observed in the electrophilic iodination of organic compounds using I 2 in appropriate solvents. , In the context of iodofluorination of α–β-unsaturated esters, it has been reported that the iodonium cation forms a covalent bond at the α-carbon position, in a similar fashion to the observations reported herein for the π-type activated TS1 of the I 2 catalyzed Michael addition reaction. Compared to other diatomic atoms in the halogen series, I 2 exhibits the lowest thermodynamic barrier for transitioning from I 2 to I – , in line with its relatively low reduction potential . Therefore, the observed conversion of I 2 to I – throughout the π-type activated Michael addition of indole to trans -crotonophenone, as documented in this study, can be considered within the expected behavior of I 2 upon interaction with the α–β-unsaturated hydrocarbon molecules.…”
Section: Resultssupporting
confidence: 75%
See 1 more Smart Citation
“…The phenomenon of I 2 forming covalent bonds with unsaturated hydrocarbon compounds is a well-established concept and has been extensively observed in the electrophilic iodination of organic compounds using I 2 in appropriate solvents. , In the context of iodofluorination of α–β-unsaturated esters, it has been reported that the iodonium cation forms a covalent bond at the α-carbon position, in a similar fashion to the observations reported herein for the π-type activated TS1 of the I 2 catalyzed Michael addition reaction. Compared to other diatomic atoms in the halogen series, I 2 exhibits the lowest thermodynamic barrier for transitioning from I 2 to I – , in line with its relatively low reduction potential . Therefore, the observed conversion of I 2 to I – throughout the π-type activated Michael addition of indole to trans -crotonophenone, as documented in this study, can be considered within the expected behavior of I 2 upon interaction with the α–β-unsaturated hydrocarbon molecules.…”
Section: Resultssupporting
confidence: 75%
“…Compared to other diatomic atoms in the halogen series, I 2 exhibits the lowest thermodynamic barrier for transitioning from I 2 to I − , in line with its relatively low reduction potential. 64 Therefore, the observed conversion of I 2 to I − throughout the π-type activated Michael addition of indole to trans-crotonophenone, as documented in this study, can be considered within the expected behavior of I 2 upon interaction with the α−β-unsaturated hydrocarbon molecules. The transitional nature of the interaction between I 2 and the αcarbon of the trans-crotonophenone serves as a driving force for the π-type activated Michael addition reaction, playing a crucial role in facilitating the transformation.…”
Section: ■ Computational Detailssupporting
confidence: 74%
“…Based on our recent work on the elucidation of sugar-NaCl-water complexes in NaCl solution 11 and the subsequent rational design of asymmetric catalysis with predictable electrostatic non-covalent interactions within chiral imine intermediates [12][13][14] , a hypothesis that the stereochemistry change of the N-arylimine moiety upon complexation with iodine could be a key for both the increase of the reactivity of the reaction, and the improvement of the enantioselectivity in previous reports, seems incredibly possible (Scheme 3B). A systematic investigation including early experimental evidences of the conformation of N-arylimines and the iodine N-arylimine complexes [15][16] , mechanisms in iodine catalysis [17][18][19] , and the structure evidences of iodine-poly(Schiff bases) complexes 20 , would be carried out in this work, to gain new insights on the mechanisms of iodine catalysis with N-arylimines.…”
Section: Introductionmentioning
confidence: 99%
“…Following our research program, which focuses on the development of TM-free 16,17 and iodine/iodide-based synthetic methods, 16,18 we present a practical method that enables the deoxygenation of pyridine N -oxides (and related species such as N -oxides derived from quinolines, isoquinolines and tertiary amines) using the I − /FA reagent. Our experimentation began exposing quinoline N -oxide ( 1a ) to KI (10% mol) in formic medium, under MW irradiation, delivering 40% yield of quinoline ( 2a ) (entry 1, Table 1).…”
mentioning
confidence: 99%