Benziodoxole-Based Hypervalent Iodine Reagents in Organic Synthesis

2005 ◽  
Vol 2 (1) ◽  
pp. 121-145 ◽  
Author(s):  
Viktor Zhdankin
Keyword(s):  
Organic Synthesis ◽  
Hypervalent Iodine

scholarly journals Sulfur-based chiral iodoarenes: An underexplored class of chiral hypervalent iodine reagents

Synthesis ◽  
2021 ◽  
Author(s):  
Mohamed Elsherbini ◽  
Arnaud Osi ◽  
Haifa Alharbi ◽  
Fatemah Karam ◽  
Thomas Wirth
Keyword(s):  
Organic Synthesis ◽  
Hypervalent Iodine

Chiral hypervalent iodine reagents are active players in modern stereoselective organic synthesis. Structurally diverse chiral hypervalent iodine reagents have been synthesised and extensively studied, but hypervalent iodine reagents containing chiral sulfur stereogenic centre are scarce and their synthesis is challenging. A small library of iodoarenes containing chiral sulfinamide and chiral sulfoximine moieties has been synthesised using commercially available reagents. The oxidation of the chiral iodoarene precursors to iodine(III) reagents was cumbersome due to facile overoxidation of the sulfoxide moiety and hence loss of chirality under various oxidation conditions. Oxidation of chiral sulfonimidoyl derivatives to the corresponding hypervalent iodine reagents was successful and led to novel sulfur-based chiral iodine(III) reagents.

Hypervalent iodine in organic synthesis: α-functionalization of carbonyl compounds

1995 ◽  
Vol 2 (2) ◽  
pp. 121-131 ◽  
Author(s):  
Om Prakash ◽  
Neena Saini ◽  
Madan P. Tanwar ◽  
Robert M. Moriarty
Keyword(s):  
Organic Synthesis ◽  
Carbonyl Compounds ◽  
Hypervalent Iodine

The aryl iodine-catalyzed organic transformation via hypervalent iodine species generated in situ

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Xuemin Li ◽  
Guangchen Li ◽  
Yifu Cheng ◽  
Yunfei Du
Keyword(s):  
Organic Synthesis ◽  
Oxidative Coupling ◽  
Hypervalent Iodine ◽  
Organic Transformations ◽  
Aryl Iodide ◽  
Oxidative Reaction ◽  
Iodine Species ◽  
Iodine Chemistry

Abstract The application of hypervalent iodine species generated in situ in organic transformations has emerged as a useful and powerful tool in organic synthesis, allowing for the construction of a series of bond formats via oxidative coupling. Among these transformations, the catalytic aryl iodide can be oxidized to hypervalent iodine species, which then undergoes oxidative reaction with the substrates and the aryl iodine regenerated again once the first cyclic cycle of the reaction is completed. This review aims to systematically summarize and discuss the main progress in the application of in situ-generated hypervalent iodine species, providing references and highlights for synthetic chemists who might be interested in this field of hypervalent iodine chemistry.

scholarly journals Electrocatalytic C–N Coupling via Anodically Generated Hypervalent Iodine Intermediates

2019 ◽  
Author(s):  
Asim Maity ◽  
Brandon L. Frey ◽  
Nathaneal Hoskinson ◽  
David Powers
Keyword(s):  
Electron Transfer ◽  
Organic Synthesis ◽  
Hypervalent Iodine ◽  
Interfacial Electron Transfer

Development of new electrosynthetic chemistry promises to impact the efficiency and sustainability of organic synthesis. Here we demonstrate that anodically generated hypervalent iodine intermediates effectively couple interfacial electron transfer with oxidative C-H/N-H coupling chemistry.

scholarly journals Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides

2012 ◽  
Vol 8 ◽  
pp. 344-348 ◽  
Author(s):  
Wei-Bing Liu ◽  
Cui Chen ◽  
Qing Zhang ◽  
Zhi-Bo Zhu
Keyword(s):  
Chemical Synthesis ◽  
Organic Synthesis ◽  
Lewis Acid ◽  
Reliable Method ◽  
Hypervalent Iodine ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Direct Preparation

A novel and reliable method for the direct preparation of 2,2-dihalo-N-phenylacetamides is reported. The key transformation involves the cleavage of a carbon–carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this method significantly expands the value of DIB as a unique and powerful tool in chemical synthesis. This protocol not only adds a new aspect to reactions that use other hypervalent iodine reagents but also provides a wide space for the synthesis of disubstituted acetamides.

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