Preparation of functionalized ketones via low temperature grignard reaction

Eberle, Marcel K.; KAHLE, G. G.

doi:10.1016/s0040-4039(00)92590-5

Cited by 51 publications

(15 citation statements)

References 4 publications

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“…over 17 h. The mixture was diluted with saturated aqueous ammonium chloride (5 mL 1-Chloroundec-10-en-5one 1d. 16 To a suspension of magnesium (0.19 g, 7.85 mmol) in THF (15 mL) at room temp., was added 6-bromo-1-hexene (1.0 mL, 7.5 mmol) slowly, and the mixture was heated to 72 ¡C. After 3 h, the mixture was allowed to cool to room temp.…”

Section: Scheme 10 Cascade Chemistry With the Ketone 19mentioning

confidence: 99%

“…We needed access to a variety of ketones to explore the effect on the cascade chemistry of the tether length between the carbonyl and the alkyl halide, and between the carbonyl and the alkene. These were prepared readily (~50% yield) by addition of Grignard reagents to acid chlorides, 16 however better yields of the ketones 1aÐd were obtained by addition of copper (I) bromide as a catalyst (Scheme 1).…”

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confidence: 99%

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Synthesis of Spirocyclic Amines by Using Dipolar Cycloadditions of Nitrones

2017

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Aliphatic ketones containing a chloride and alkene were heated with hydroxylamine to promote cascade, tandem condensation to oximes, cyclization to nitrones, and 1,3-dipolar cycloaddition to tricyclic isoxazolidines as single stereoisomers. Single regioisomers were obtained when three atoms linked the ketone and dipolarophile to give five-membered rings but mixtures resulted with four atoms in the tether unless a terminal ester was located on the alkene. The N-O bond in the products could be reduced to give spirocyclic amines and diamines.

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Section: Scheme 10 Cascade Chemistry With the Ketone 19mentioning

confidence: 99%

mentioning

confidence: 99%

Synthesis of Spirocyclic Amines by Using Dipolar Cycloadditions of Nitrones

2017

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“…The nucleophilic addition of acyl halides with organometallic reagents such as organomagnesium, organozinc, organocadmium and organocopper compounds is an extremely useful tool for the synthesis of ketones . These protocols often proceed in low yield because of the addition of the organometallic reagent to the ketone to form tertiary alcohols …”

Section: Introductionmentioning

confidence: 99%

Fabrication of covalently functionalized mesoporous silica core–shell magnetite nanoparticles with palladium(II) acetylacetonate: application as a magnetically separable nanocatalyst for Suzuki cross‐coupling reaction of acyl halides with boronic acids

Hajipour

Azizi

2015

Applied Organom Chemis

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aWe report the preparation of supported palladium(II) acetylacetonate, Pd(acac) 2 , coordinated by pendant acac groups, by reacting palladium acetate with acac-functionalized doubly silica-coated magnetic nanoparticles. The solid support consists of an amorphous silica-coated (as magnetite protecting layer) magnetite core and a mesoporous silica shell. The magnetically separable palladium nanocatalyst is active for Suzuki cross-coupling reaction of acyl halides with boronic acids. The catalyst is simply isolated from the reaction mixture that allows fast and efficient isolation of product and catalyst compared to traditional methods that generally make use of time-and solvent-consuming procedures.

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“…However, the reaction is incompatible with many functional groups and delivers limited para‐regioselectivity. Organometallic species such as Grignard and organozinc reagents also promote the synthesis of ketones from acid chlorides or esters, but a strong affinity of these reagents towards product ketone produces tertiary alcohol as a side product . In 1993, Suzuki reported another potent method for the synthesis of biaryl ketones using aryl halide, using carbon monoxide in the presence of palladium catalyst, which later became modified into many versatile and elegant protocols .…”

Section: Introductionmentioning

confidence: 99%

Ligandless heterogeneous palladium: an efficient and recyclable catalyst for Suzuki‐type cross‐coupling reaction

Mondal

Bora

2014

Applied Organom Chemis

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A mild and efficient ligand‐free Suzuki‐type cross‐coupling reaction of benzoyl chlorides and arylboronic acids catalyzed by heterogeneous Pd/C was developed. Benzoyl chlorides undergo cross‐coupling with electronically diverse arylboronic acids to give biaryl ketones in excellent yield, under aqueous media and optimum temperature. The application of 3 mol% of 10 wt% Pd/C to the cross‐coupling delivers utmost efficiency, and could be reused up to many consecutive cycles without any loss in activity. This method proceeds under aqueous media and a recyclable catalytic system, offering an environmentally benign alternative to the existing protocols. Copyright © 2014 John Wiley & Sons, Ltd.

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Preparation of functionalized ketones via low temperature grignard reaction

Cited by 51 publications

References 4 publications

Synthesis of Spirocyclic Amines by Using Dipolar Cycloadditions of Nitrones

Synthesis of Spirocyclic Amines by Using Dipolar Cycloadditions of Nitrones

Fabrication of covalently functionalized mesoporous silica core–shell magnetite nanoparticles with palladium(II) acetylacetonate: application as a magnetically separable nanocatalyst for Suzuki cross‐coupling reaction of acyl halides with boronic acids

Ligandless heterogeneous palladium: an efficient and recyclable catalyst for Suzuki‐type cross‐coupling reaction

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