A new and versatile one-pot strategy to synthesize alpha-bromoketones from secondary alcohols using ammonium bromide and oxone

Banothu, Rammurthy; Swamy, Peraka; Mameda, Naresh; Kodumuri, Srujana; Chevella, Durgaiah; Gajula, Krishna Sai; Narender, Nama

doi:10.1039/c7nj00052a

Cited by 13 publications

(11 citation statements)

References 60 publications

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“…α-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] TMSenolates [68] or ketones, [69] etc. We showed that olefins can Scheme 17 Proposed mechanism for Oxidative Cleavage of an Olefin by in situ-Generated Catalyst 5. be converted to α-bromoketones by treatment with NBS in the presence of IBX in DMSO.…”

Section: One-pot Transformation Of Olefins To α-Bromo-and α-Azidoketonesmentioning

confidence: 99%

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 To α-Bromo-and α-Azidoketonesmentioning

confidence: 99%

Catalytic Oxidations with ortho-Substituted Modified IBXs

Parida

Moorthy

2022

Synlett

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“…and Oxone ® (3 equiv.) [ 166 ]. This altered procedure yielded 10 α-bromoketones in low to excellent yields (38–94%).…”

Section: Oxidative Halogenation Of Secondary Alcoholsmentioning

confidence: 99%

Synthetic Access to Aromatic α-Haloketones

et al. 2022

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α-Haloketones play an essential role in the synthesis of complex N-, S-, O-heterocycles; of which some exhibit a remarkable biological activity. Research further illustrated that α-bromo-, α-chloro-, and α-iodoketones are key precursors for blockbuster pharmacological compounds. Over the past twenty years, substantial advances have been made in the synthesis of these industrially relevant building blocks. Efforts have focused on rendering the synthetic protocols greener, more effective and versatile. In this survey, we summarised and thoroughly evaluated the progress of the field, established in the past two decades, in terms of generality, efficacy and sustainability.

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“…On the other hand, an efficient and green protocol for the synthesis of α-bromoketones 179 a-i from secondary alcohols 178 using non-toxic reagent such as NH 4 Br/oxone in the presence of MeOH/H 2 O solvent mixture was developed by Rammurthy et al in 2017 as shown in the Scheme 56. [151] This reaction occurs in two consecutive steps first oxidation of secondary alcohol to ketones followed by the oxidative bromination of thus formed ketone derivatives to afford the required α-bromoketone products. A proposed mechanism for the formation of α-bromoketones from the starting alcohols is clearly presented in the Scheme 57.…”

Section: Chemistryselectmentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Presently, the major cornerstone of the research community is to develop green as well as sustainable protocols involving inexpensive catalysts and/or reagents without the usage of hazardous solvents under globally friendlier conditions in order to shelter both mankind and environment. Therefore, needless to say, there is always a supreme need to surrogate the older, costlier and unsafe strategies with the novel economically inexpensive and environmental benign ones. To this context, in recent past, oxone® (triple salt), a very cheap oxidizing agent having the chemical formula 2KHSO5 ⋅ KHSO4 ⋅ K2SO4 and enwrapped with the unique characteristics like easy handling, non‐toxic, safe, eco‐friendly, non‐polluting, stable, and nicely soluble in water, in addition to its utility for large‐scale synthesis etc. Bearing the importance of this versatile reagent in mind, we envisioned to update the recent advances made in this direction. Consequently, in this particular review article, the developments made in the arena of oxone chemistry covering from 2013 to 2020 have been revealed as no report appeared in the literature after a wonderful Chem. Rev. published by the group of Hussain in 2013. Herein, a comprehensive detail of a variety of oxidative transformations along with the complete plausible mechanistic steps have been exposed. For sure, present review would be a very helpful tool to the scientific community not only working in the area of organic synthesis but also to the researchers working in other branches of science and technologies as well.

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A new and versatile one-pot strategy to synthesize alpha-bromoketones from secondary alcohols using ammonium bromide and oxone

Abstract: A new, efficient and green protocol for the one-pot synthesis of alpha-bromoketones from secondary alcohols is reported.

Cited by 13 publications

References 60 publications

Catalytic Oxidations with ortho-Substituted Modified IBXs

Catalytic Oxidations with ortho-Substituted Modified IBXs

Synthetic Access to Aromatic α-Haloketones

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

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