Advances in Synthetic Applications of Hypervalent Iodine Compounds
Top Cited Papers
- 10 February 2016
- journal article
- Published by American Chemical Society (ACS) in Chemical Reviews
- Vol. 116 (5), 3328-3435
- https://doi.org/10.1021/acs.chemrev.5b00547
Abstract
The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C-C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.Keywords
Funding Information
- Division of Chemistry (CHE-035354, CHE-0702734, CHE-1009038, CHE-1262479)
This publication has 100 references indexed in Scilit:
- Ethynylbenziodoxolones (EBX) as Reagents for the Ethynylation of Stabilized EnolatesAdvanced Synthesis & Catalysis, 2013
- A Palladium‐Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)‐TrachelanthamidineAngewandte Chemie, 2011
- A Versatile and Highly Reactive Polyfluorinated Hypervalent Iodine(III) CompoundAngewandte Chemie, 2010
- Various α‐Oxygen Functionalizations of β‐Dicarbonyl Compounds Mediated by the Hypervalent Iodine(III) Reagent p‐Iodotoluene Difluoride with Different Oxygen‐Containing NucleophilesAdvanced Synthesis & Catalysis, 2010
- Concise One‐Pot Tandem Synthesis of Indoles and Isoquinolines from AmidesAngewandte Chemie, 2009
- Total Synthesis of TK‐57‐164A, Isariotin F, and Their Putative Progenitor Isariotin EAngewandte Chemie, 2009
- One‐Pot Synthesis of Carbamoyl Azides Directly from Primary Alcohols and Oxidation of Secondary Alcohols to Ketones Using Iodobenzene Dichloride in Combination with Sodium AzideAdvanced Synthesis & Catalysis, 2009
- Mechanochemical Aminochlorination of Electron‐Deficient Olefins with Chloramine‐T Promoted by (Diacetoxyiodo)benzeneAdvanced Synthesis & Catalysis, 2007
- Domino Reaction of 2,3‐Epoxy‐1‐alcohols and PIFA in the Presence of H2O and the Concise Synthesis of (+)‐TanikolideAngewandte Chemie, 2005
- Reagents with Hypervalent Iodine: Formation of Convenient Chiral Synthetic Intermediates by Fragmentation of Carbohydrate Anomeric Alkoxy RadicalsAngewandte Chemie, 1992