Catalytic Oxidations with ortho-Substituted Modified IBXs

Keshaba N. Parida; Jarugu Narasimha Moorthy

doi:10.1055/a-1813-7319

Synlett, Table of Contents

Synlett 2023; 34(06): 495-506
DOI: 10.1055/a-1813-7319

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Chemical Synthesis and Catalysis in India

Catalytic Oxidations with ortho-Substituted Modified IBXs

Keshaba N. Parida∗

^aSchool of Chemistry, IISER Thiruvananthapuram, Maruthamala, PO- Vithura, Kerala 695551, India

,

Jarugu Narasimha Moorthy ∗

^aSchool of Chemistry, IISER Thiruvananthapuram, Maruthamala, PO- Vithura, Kerala 695551, India

^bDepartment of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India

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Abstract

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Abstract

o-Iodoxybenzoic acid (IBX) is an oxidation reagent that has surged into prominence in the last two decades. It is cost-effective, environmentally benign, and readily prepared from o-iodobenzoic acid. However, its insolubility in common organic solvents and explosive attributes upon impact and heating are debilitating disadvantages. The development of modified IBXs (mIBXs) that exhibit improved solubility and enhanced reactivity, and obviate explosive attributes by judicious manipulation of the structure of IBX has been an incessant endeavor. In this account, common organic solvent-soluble mIBXs developed in our research group are collated with a discussion of the rationale underlying the design principles. Steric build-up around the iodoxolone moiety that is responsible for strong intermolecular interactions within the crystal lattice of IBX constitutes the key consideration in the design and development of modified λ⁵-iodanes that are reactive and sparingly soluble in common organic solvents. In situ generation of mIBXs from precursor iodo-acids in the presence of Oxone^® permits their employment as organocatalysts for facile oxidative transformations. Reactive mIBXs generated in situ from precursor modified iodo-acids (mIAs, I^I) in the presence of Oxone^® may offer unrivaled prospects for cost-effective oxidations. Applications of mIBXs, generated in situ or otherwise, for efficient oxidations are consolidated.

1 Introduction

2 Design and Synthesis of Modified IBXs and their Precursors Iodo-Acids

3 Catalytic Oxidations with Modified IBXs

3.1 Oxidation of Alcohols

3.2 Oxidation of 1,2-Diols

3.3 Conversion of Diols into Lactones

3.4 One-Pot Oxidative Cleavage of Olefins

3.5 One-Pot Transformation of Olefins into α-Bromo- and α-Azidoketones

4 Conclusions

Key words

IBX - Oxone^® - alcohols - oxidative cleavage - α-bromoketones - lactones - α-azidoketones

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