Direct Conversion of Olefins into α-Bromo Ketones Using O-Iodoxybenzoic Acid and Tetraethylammonium Bromide

Deshmukh, Swapnil S.; Chaudhari, Kiran H.; Akamanchi, Krishnacharya G.

doi:10.1055/s-0030-1259090

Cited by 1 publication

(2 citation statements)

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“…-Bromoketones are important intermediates in the synthesis of various complex molecules. [64][65][66] These 1,2-synthons can be typically accessed from alkenes, 66 alcohols, 67 TMS-enolates, 68 and ketones. 69 We showed that olefins can be converted into -bromoketones by treatment with NBS in the presence of IBX in DMSO.…”

Section: One-pot Transformation Of Olefins Into -Bromo-and -Azidoke...mentioning

confidence: 99%

“…To obviate the use of DMSO, the reaction with IBX (1 equiv) was carried out with tetraethylammonium bromide (TEAB, 1 equiv) as a brominating reagent in anhydrous CH 2 Cl 2 at room temperature. 66 The catalytic protocol avoids stoichiometric usage of IBX and replaces the polar and high-boiling DMSO as the solvent. Accordingly, the cat-…”

Section: One-pot Transformation Of Olefins Into -Bromo-and -Azidoke...mentioning

confidence: 99%

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Catalytic Oxidations with ortho-Substituted Modified IBXs

Parida

Moorthy

2022

Synlett

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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. Development of modified IBXs,i.e., mIBXs, that exhibit improved solubility and enhanced reactivity, and obviate explosive attributes by a judicious manipulation of the structure of IBX has been an incessant endeavor. In this account, common organic solvent-soluble modified o-iodoxybenzoic acids (mIBXs) developed in our research group are collated with discussion of 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 employment of the latter as organocatalysts for facile oxidative transformations. Reactive mIBXs generated in situ from precursor modified iodoacids (mIAs, I(I)) in the presence of Oxone® may constitute unrivaled prospects for cost-effective oxidations. Applications of mIBXs, generated in situ or otherwise, for efficient oxidations are consolidated.

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Section: One-pot Transformation Of Olefins Into -Bromo-and -Azidoke...mentioning

confidence: 99%

Section: One-pot Transformation Of Olefins Into -Bromo-and -Azidoke...mentioning

confidence: 99%

Catalytic Oxidations with ortho-Substituted Modified IBXs

Parida

Moorthy

2022

Synlett

View full text Add to dashboard Cite

show abstract

Direct Conversion of Olefins into α-Bromo Ketones Using O-Iodoxybenzoic Acid and Tetraethylammonium Bromide

Abstract: Utilizing full potential of IBX, a mild, selective, and facile method has been developed for the direct conversion of olefins into the corresponding a-bromo ketones by using 1.1 equivalents each of o-iodoxybenzoic acid and tetraethylammonium bromide.

Cited by 1 publication

References 7 publications

Catalytic Oxidations with ortho-Substituted Modified IBXs

Catalytic Oxidations with ortho-Substituted Modified IBXs

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