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Literature DB >> 27629653

Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents.

Elin Stridfeldt¹, Alexandra Seemann¹, Marinus J Bouma¹, Chandan Dey¹, Anne Ertan², Berit Olofsson³.

Abstract

A novel type of hypervalent iodine(III) reagents, vinylbenziodoxolones (VBX), has been synthesized in a one-pot reaction from 2-iodobenzoic acid. VBX is bench stable, has been thoroughly characterized and the cyclic structure is supported by X-ray analysis. The reactivity of VBX was investigated in vinylation of nitrocyclohexane, and delivered vinylated products with opposite regioselectivity compared to acyclic vinyl(aryl)iodonium salts. The reagents could become a powerful tool in vinylation reactions under both metal-free and metal-catalyzed conditions.

Entities: Chemical

Keywords: benziodoxolones; hypervalent compounds; structure analysis; synthetic methods; vinylation

Year: 2016 PMID： 27629653 DOI： 10.1002/chem.201603955

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

7 in total

1. Light-Driven Intermolecular Charge Transfer Induced Reactivity of Ethynylbenziodoxol(on)e and Phenols.

Authors: Bin Liu; Chern-Hooi Lim; Garret M Miyake
Journal: J Am Chem Soc Date: 2018-10-02 Impact factor: 15.419

Review 2. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors: Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal: Chem Rev Date: 2021-10-08 Impact factor: 60.622

Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents.

1. Light-Driven Intermolecular Charge Transfer Induced Reactivity of Ethynylbenziodoxol(on)e and Phenols.

Review 2. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

3. Ritter-type iodo(iii)amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides.

4. Explaining Regiodivergent Vinylations with Vinylbenziodoxolones.

5. Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers.

6. Photoredox Imino Functionalizations of Olefins.

7. Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions.