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Literature DB >> 16218584

Enhancing 2-iodoxybenzoic acid reactivity by exploiting a hypervalent twist.

Abstract

A rearrangement of hypervalent bonds, or twisting, proves to be the rate-determining step in the 2-iodoxybenzoic acid (IBX) oxidation of alcohols. From this insight, derived from density functional theory calculations, we explain why IBX oxidizes large alcohols faster than small ones and propose a modification to the reagent predicted to make it more active.

Entities: Chemical

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Year: 2005 PMID： 16218584 DOI： 10.1021/ja054446x

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

7 in total

Review 1. Chemistry of polyvalent iodine.

Authors: Viktor V Zhdankin; Peter J Stang
Journal: Chem Rev Date: 2008-12 Impact factor: 60.622

2. A theoretical study on diastereoselective oxidative dearomatization by iodoxybenzoic acid.

Authors: Vincent Tognetti; Agathe Boulangé; Philippe A Peixoto; Xavier Franck; Laurent Joubert
Journal: J Mol Model Date: 2014-07-20 Impact factor: 1.810

3. Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Authors: Andrew M Harned
Journal: Tetrahedron Lett Date: 2014-08-20 Impact factor: 2.415

4. Oxidation of Electron-Deficient Phenols Mediated by Hypervalent Iodine(V) Reagents: Fundamental Mechanistic Features Revealed by a Density Functional Theory-Based Investigation.

Authors: Mona Jalali; Alex C Bissember; Brian F Yates; Sarah E Wengryniuk; Alireza Ariafard
Journal: J Org Chem Date: 2021-08-19 Impact factor: 4.198

Enhancing 2-iodoxybenzoic acid reactivity by exploiting a hypervalent twist.

Review 1. Chemistry of polyvalent iodine.

2. A theoretical study on diastereoselective oxidative dearomatization by iodoxybenzoic acid.

3. Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

4. Oxidation of Electron-Deficient Phenols Mediated by Hypervalent Iodine(V) Reagents: Fundamental Mechanistic Features Revealed by a Density Functional Theory-Based Investigation.

5. Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp³)-H Bonds with Zhdankin's λ³-Azidoiodane.

6. Bidentate Nitrogen-Ligated I(V) Reagents, Bi(N)-HVIs: Preparation, Stability, Structure, and Reactivity.

7. Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights.

Enhancing 2-iodoxybenzoic acid reactivity by exploiting a hypervalent twist.

Review 1. Chemistry of polyvalent iodine.

2. A theoretical study on diastereoselective oxidative dearomatization by iodoxybenzoic acid.

3. Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

4. Oxidation of Electron-Deficient Phenols Mediated by Hypervalent Iodine(V) Reagents: Fundamental Mechanistic Features Revealed by a Density Functional Theory-Based Investigation.

5. Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp3)-H Bonds with Zhdankin's λ3-Azidoiodane.

6. Bidentate Nitrogen-Ligated I(V) Reagents, Bi(N)-HVIs: Preparation, Stability, Structure, and Reactivity.

7. Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights.

5. Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp³)-H Bonds with Zhdankin's λ³-Azidoiodane.