The Chemistry of α‐Haloketones and Their Utility in Heterocyclic Synthesis

Erian, A. W.; Sherif, Sherif M.; Gaber, Hatem M.

doi:10.1002/chin.200517273

Cited by 3 publications

(3 citation statements)

References 332 publications

(340 reference statements)

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“…Oxidative iodination of ketones with Eco-Mn 2 Halogenated compounds are widely used as chemical precursors in a number of reactions (Meijere and Diederich 2004). In particular, α-iodinated ketones exhibit great reactivity and give access to a large set of compounds, including heterocycles with pharmacological activity (Erian et al 2003).…”

Section: Examples Of Eco-mn 2 -Promoted Oxidationsmentioning

confidence: 99%

Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants

Escande

Renard

Grison

2014

Environ Sci Pollut Res

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Among the phytotechnologies used for the reclamation of degraded mining sites, phytoextraction aims to diminish the concentration of polluting elements in contaminated soils. However, the biomass resulting from the phytoextraction processes (highly enriched in polluting elements) is too often considered as a problematic waste. The manganese-enriched biomass derived from native Mn-hyperaccumulating plants of New Caledonia was presented here as a valuable source of metallic elements of high interest in chemical catalysis. The preparation of the catalyst Eco-Mn1 and reagent Eco-Mn2 derived from Grevillea exul exul and Grevillea exul rubiginosa was investigated. Their unusual polymetallic compositions allowed to explore new reactivity of low oxidative state of manganese-Mn(II) for Eco-Mn1 and Mn(IV) for Eco-Mn2. Eco-Mn1 was used as a Lewis acid to catalyze the acetalization/elimination of aldehydes into enol ethers with high yields; a new green and stereoselective synthesis of (-)-isopulegol via the carbonyl-ene cyclization of (+)-citronellal was also performed with Eco-Mn1. Eco-Mn2 was used as a mild oxidative reagent and controlled the oxidation of aliphatic alcohols into aldehydes with quantitative yields. Oxidative cleavage was interestingly noticed when Eco-Mn2 was used in the presence of a polyol. Eco-Mn2 allowed direct oxidative iodination of ketones without using iodine, which is strongly discouraged by new environmental legislations. Finally, the combination of the properties in the Eco-Mn catalysts and reagents gave them an unprecedented potential to perform sequential tandem oxidation processes through new green syntheses of p-cymene from (-)-isopulegol and (+)-citronellal; and a new green synthesis of functionalized pyridines by in situ oxidation of 1,4-dihydropyridines.

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Section: Examples Of Eco-mn 2 -Promoted Oxidationsmentioning

confidence: 99%

Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants

Escande

Renard

Grison

2014

Environ Sci Pollut Res

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“…23,24 They are, in particular, unusually fast, [25][26][27][28][29][30][31] though how much so depends on the nucleophile and other circumstances. [32][33][34][35][36][37][38][39][40] Various mechanistic reasons have been proposed for this. Some authors argue that addition takes place initially at the carbonyl, followed by either a 1,2-shi of the nucleophile to the alpha position, [41][42][43][44][45][46][47] or, alternatively, formation of an epoxide that reacts with further nucleophile at the alpha position.…”

Section: Introductionmentioning

confidence: 99%

Bromo–nitro substitution on a tertiary α carbon—a previously uncharacterized facet of the Kornblum substitution

2015

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“…𝛼𝛼-Haloketones have been attracting increasing attention in view of their high reactivity as building blocks for the preparation of compounds of various classes due to their selective transformations with different reagents [41]. e sulfonation of 𝛼𝛼-haloketones involves the displacement reaction of halogens with sul�nic acid salts.…”

Section: Introductionmentioning

confidence: 99%

Comparative Studies on Conventional and Ultrasound‐Assisted Synthesis of Novel Homoallylic Alcohol Derivatives Linked to Sulfonyl Dibenzene Moiety in Aqueous Media

Mady

El-Kateb

Zeid

et al. 2012

Journal of Chemistry

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Novel homoallylic alcohols incorporating sulfone moieties were synthesized by the treatment of different carbonyl compounds with allylic bromides in aqueous mediaviasonochemical Barbier-type reaction conditions. Sulfonation ofα-bromoketones with sodium benzenesulfinate in presence of CuI/2,6-lutidine rapidly gaveβ-keto-sulfones in good yields. In general, ultrasound irradiation offered the advantages of high yields, short reaction times, and simplicity compared to the conventional methods. The structures of all the compounds were confirmed by analytical and spectral data.

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The Chemistry of α‐Haloketones and Their Utility in Heterocyclic Synthesis

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 3 publications

References 332 publications

Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants

Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants

Bromo–nitro substitution on a tertiary α carbon—a previously uncharacterized facet of the Kornblum substitution

Comparative Studies on Conventional and Ultrasound‐Assisted Synthesis of Novel Homoallylic Alcohol Derivatives Linked to Sulfonyl Dibenzene Moiety in Aqueous Media

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