Copper-, ligand- and solvent-free synthesis of ynones by coupling acid chlorides with terminal alkynes

Palimkar, Sanjay S.; Kumar, Pradeep; Jogdand, Nivrutti R.; Daniel, Thomas; Lahoti, R. J.; Srinivasan, Kumar

doi:10.1016/j.tetlet.2006.05.166

Cited by 60 publications

(19 citation statements)

References 13 publications

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“…[3][4][5][6][7][8][9][10][11][12][13][14][15] Propargylic alcohols have also been used in the syntheses of biologically active compounds [16] such as anticancer agents [17] and nucleosides. [18] In addition to the oxidation of propargylic alcohols, the direct α-oxidation of alkynes to the corresponding ketones [19][20][21] and some other methods that use a terminal alkyne as a building block [22][23][24][25][26][27][28][29][30] have also been reported for the preparation of α,β-acetylenic ketones.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Propargylic Alcohols with a 2‐Quinoxalinol Salen Copper(II) Complex and tert‐Butyl Hydroperoxide

Weerasiri

Gorden

2013

Eur J Org Chem

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The copper(II) complex of 2-quinoxalinol salen (salqu) is an efficient catalyst for the selective oxidation of propargylic alcohols to yield the corresponding α,β-acetylenic carbonyl compounds when used in combination with the oxidant tertbutyl hydroperoxide (TBHP). Excellent yields (up to 99 %) are achieved for a variety of propargylic alcohols within 1 h of reaction time. The (salqu)copper(II) complex with TBHP[a]

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Section: Introductionmentioning

confidence: 99%

Oxidation of Propargylic Alcohols with a 2‐Quinoxalinol Salen Copper(II) Complex and tert‐Butyl Hydroperoxide

Weerasiri

Gorden

2013

Eur J Org Chem

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“…The efficiency of the conversion of the electron-deficient acyl chloride 34 decreased in the presence of NCy 2 Me (Entries 4 and 8). Copper- and solvent-free reaction conditions 28 also lowered yields (Entries 9 and 10).…”

Section: Resultsmentioning

confidence: 99%

Condensation reactions of guanidines with bis-electrophiles: formation of highly nitrogenous heterocycles

Arnold¹,

LaPorte²,

Anderson³

et al. 2013

Tetrahedron

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2-Amino-1,4-dihydropyrimidines were reacted with bis-electrophiles to produce novel fused bi-pyrimidine, pyrimido-aminotriazine, and pyrimido-sulfonamide scaffolds. In addition, a quinazoline library was constructed using a guanidine Atwal-Biginelli reaction with 1-(quinazolin-2-yl)guanidines. The product heterocycles have novel constitutions with high nitrogen atom counts and represent valuable additions to screening libraries for the discovery of new modulators of biological targets.

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“…Even if PdCl 2 (PPh 3 ) 2 /CuI are the most employed catalysts for acyl Sonogashira reactions, some other palladium species have been tested in this coupling. In particular, Srinivasan's group [36,37] developed a cross-coupling between acid chlorides and terminal acetylenes promoted by 0.2 mol % of Pd(OAc) 2 and performed under solvent-free conditions at room temperature. After 10 min, quantitative conversion into the expected alkynones was observed in almost all cases.…”

Section: Pd(oac) 2 Catalysed Acyl Sonogashira Reactionsmentioning

confidence: 99%

Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds

Albano

Aronica

2019

Catalysts

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The acyl Sonogashira reaction represents an extension of Sonogashira cross-coupling to acid chlorides which replace aryl or vinyl halides, while terminal acetylenes are used as coupling partners in both reactions. The introduction of a carbonyl functional group on the alkyne backbone determines a radical change in the reactivity of the products. Indeed, α,β-alkynyl ketones can be easily converted into different heterocyclic compounds depending on the experimental conditions employed. Due to its potential, the acyl Sonogashira reaction has been deeply studied with particular attention to the nature of the catalysts and to the structures of both coupling compounds. Considering these two aspects, in this review, a detailed analysis of the literature data regarding the acyl Sonogashira reaction and its role in the synthesis of several heterocyclic derivatives is reported.

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Copper-, ligand- and solvent-free synthesis of ynones by coupling acid chlorides with terminal alkynes

Cited by 60 publications

References 13 publications

Oxidation of Propargylic Alcohols with a 2‐Quinoxalinol Salen Copper(II) Complex and tert‐Butyl Hydroperoxide

Oxidation of Propargylic Alcohols with a 2‐Quinoxalinol Salen Copper(II) Complex and tert‐Butyl Hydroperoxide

Condensation reactions of guanidines with bis-electrophiles: formation of highly nitrogenous heterocycles

Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds

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