Synthesis and Structures of Novel Chiral Cyclic Hypervalent Iodine(III) Reagents for Metal‐Free Ligand‐Transfer Reactions
- 1Univ. Bordeaux ISM (CNRS‐UMR 5255) Talence Cedex France
- 2CNRS/UNIV PAU & PAYS ADOUR IPREM (CNRS‐UMR 5254) Pau Cedex France
Abstract
The preparation of novel chiral λ 3 ‐iodane reagents bearing transferable halogen‐, oxygen‐ or carbon‐based ligands is described. Among these hypervalent iodine(III)‐based compounds are (i) the first chiral bis(cyano‐λ 3 ‐iodane), whose bis(benziodazolone) structure is derived from an enantiopure cyclohexyldiamine‐based bis(amidoiodoarene), and (ii) the two first chiral benziodoxolones bearing a carbon‐based ligand (i.e., cyano and trifluoromethyl groups) together with a lactate moiety ortho ‐positioned to the iodine(III) atom. The proposed iodine‐containing heterocyclic structures of these new λ 3 ‐iodanes are supported by x‐ray diffraction analyses and DFT calculations. Their capacity to transfer their ligand(s) in an asymmetric fashion to different substrates (i.e., β‐ketoesters, naphthols, and oxindoles) was also examined.
Related
- Mechanochemical synthesis using hypervalent iodine reagents
- Electrifying Oxygen Atom Transfer Reactions: Utilizing OER and ORR Pathways for Organic Synthesis
- Cobalt Photocatalyzed Carbonylation Reactions in Flow: From Mass-Transfer to Light-Limited Regimes
- Iron-Catalyzed Nitrene Transfer Reactions Enabled by Hydroxylamine Derivatives.
- Auto‐Click Synthesis of a Copper(I) –N ‐Heterocyclic Carbene Porous Organic Polymer and Its Transmetalation to Palladium(II) for Azide–Alkyne Cycloaddition and Cross‐Coupling Reactions
BibTeX
@article{valzer2026synthesis,
title = {{Synthesis and Structures of Novel Chiral Cyclic Hypervalent Iodine(III) Reagents for Metal‐Free Ligand‐Transfer Reactions}},
author = {Emmanuel Valzer and Jean‐Marc Sotiropoulos and Karinne Miqueu and Laurent Pouységu and Stéphane Quideau},
journal = {Chemistry - A European Journal},
year = {2026},
month = aug,
doi = {10.1002/chem.71441},
url = {https://univ-pau.hal.science/hal-05778292v1},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Synthesis and Structures of Novel Chiral Cyclic Hypervalent Iodine(III) Reagents for Metal‐Free Ligand‐Transfer Reactions
AU - Emmanuel Valzer
AU - Jean‐Marc Sotiropoulos
AU - Karinne Miqueu
AU - Laurent Pouységu
AU - Stéphane Quideau
PY - 2026
DA - 2026/08/04
JO - Chemistry - A European Journal
DO - 10.1002/chem.71441
UR - https://univ-pau.hal.science/hal-05778292v1
AB - The preparation of novel chiral λ 3 ‐iodane reagents bearing transferable halogen‐, oxygen‐ or carbon‐based ligands is described. Among these hypervalent iodine(III)‐based compounds are (i) the first chiral bis(cyano‐λ 3 ‐iodane), whose bis(benziodazolone) structure is derived from an enantiopure cyclohexyldiamine‐based bis(amidoiodoarene), and (ii) the two first chiral benziodoxolones bearing a carbon‐based ligand (i.e., cyano and trifluoromethyl groups) together with a lactate moiety ortho ‐positioned to the iodine(III) atom. The proposed iodine‐containing heterocyclic structures of these new λ 3 ‐iodanes are supported by x‐ray diffraction analyses and DFT calculations. Their capacity to transfer their ligand(s) in an asymmetric fashion to different substrates (i.e., β‐ketoesters, naphthols, and oxindoles) was also examined.
SN - 0947-6539
SN - 1521-3765
ER -