Catalytic high pressure synthesis of hindered β-aminoesters

Jenner, G.

doi:10.1016/0040-4039(94)02215-w

Cited by 120 publications

(40 citation statements)

References 13 publications

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“…The catalysis proceeds by the r-alkylpalladium complex following b-elimination to give an unstable palladium hydride complex [4]. Further, Yb(OTf) 3 catalyzed hydroamination of a,bunsaturated esters with benzylamine also gave the antiMarkovnikov adducts via conjugate addition of amine [8][9][10][11]. However there are no reports to discuss the preferential formation of anti-Markovnikov adducts in hydroamination of a,b-unsaturated esters with amine.…”

Section: Mechanistic Aspects Of the Hydroaminationmentioning

confidence: 93%

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The Hydroamination of methyl acrylates with amines over zeolites

et al. 2005

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H-form zeolites, H-FAU and H-BEA have been studied as heterogeneous catalysts for the hydroamination. They catalyzed the reaction of methyl acrylate with aniline to give N-[2-(methoxycarbonyl)ethyl]aniline (1) as a main product. H-BEA and H-FAU zeolites efficiently catalyzed the hydroamination to afford anti-Markovnikov adduct as a main product. The conversion of aniline around 55-85% was achieved within 18 h over H-BEA and H-FAU zeolites with SiO 2 /Al 2 O 3 molar ratio of 25-30; however, the formation of N,N-bis[2-(methoxycarbonyl)ethyl]aniline (2) as a product of double addition of methyl acrylate to aniline has also been observed as a by-product over H-BEA and H-FAU catalysts. The influences of the reaction parameters such as temperature and catalyst amount, and type of a,b-unsaturated esters and amines have been also investigated.

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Section: Mechanistic Aspects Of the Hydroaminationmentioning

confidence: 93%

“…Recently, there have been several reports on the hydroamination of aniline catalyzed by transition metals such as palladium [2][3][4], ruthenium [5], nickel [6], and rhodium [7]. It was also possible to perform the hydroamination of acrylic acid derivatives with cyclic amines [2,6,[8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

The Hydroamination of methyl acrylates with amines over zeolites

et al. 2005

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“…It represents a valuable synthetic alternative to the established Mannich reaction (Scheme 1b). Under bulk solution-phase conditions, the azaMichael addition is catalyzed by Lewis acids [2,3] (under strictly anhydrous conditions), metal catalysts [4][5][6] [e.g., Yb(OTf) 3 , InCl 3 , FeCl 3 .7H 2 O/CO(OAc) 2 ], oxidizing agents [7,8] (e.g., ceric ammonium nitrate) or N-heterocyclic carbenes [9] generated by treating imidazolium salts with a base). In this study, interfacial versions of the aza-Michael addition and Mannich reactions were carried out under ambient conditions in high yields (on a small scale) without the use of catalyst.…”

Section: Introductionmentioning

confidence: 99%

Accelerated C–N Bond Formation in Dropcast Thin Films on Ambient Surfaces

Badu‐Tawiah

Campbell

Cooks

2012

J. Am. Soc. Mass Spectrom.

112

109

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The aza-Michael addition and the Mannich condensation occur in thin films deposited on ambient surfaces. The reagents for both C-N bond formation reactions were transferred onto the surface by drop-casting using a micropipette. The surface reactions were found to be much more efficient than the corresponding bulk solution-phase reactions performed on the same scale in the same acetonitrile solvent. The increase in rate of product formation in the thin film is attributed to solvent evaporation in the open air which results in reagent concentration and produces rate acceleration similar to that seen in evaporating droplets in desorption electrospray ionization. This thin film procedure has potential for the rapid synthesis of reaction products on a small scale, as well as allowing rapid derivatization of analytes to produce forms that are easily ionized by electrospray ionization. Analysis of the derivatized sample directly from the reaction surface through the use of desorption electrospray ionization is also demonstrated.

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“…Moreover, most Lewis acid catalysts are likely to be poisoned by alkyl and arylamine reagents [12]. In order to overcome some of these limitations, a number of alternative procedures have been reported over the past few years using a variety of catalysts such as PdCl 2 (MeCN) 2 [13], InCl 3 [14], CeCl 3 Á7H 2 O [15], Yb(OTf) 3 [16,17], SmI 2 [18], Cu(OTf) 2 [19,20], Bi(NO 3 ) 2 [21], LiClO 4 [22], TMSCl [23], Boric acid [24], Borax [25], and acidic solids [26]. Heterogeneous solid salts [22,27], fluoride [27], ionic liquid [28], b-cyclodextrin [29], and sodium dodecylsulfate (SDS) [30] have also been used for this transformation.…”

mentioning

confidence: 99%

Phosphate Impregnated Titania: An Efficient Reusable Heterogeneous Catalyst for Aza-Michael Reactions Under Solvent-Free Condition

Nath

Chaudhuri

2009

Catal Lett

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The aza-Michael reactions of amines with a,bunsaturated compounds have efficiently been carried out using phosphate impregnated titania containing 84.5% of TiO 2 and 15.5% of [Ti 4 H 11 (PO 4 ) 9 ]ÁnH 2 O (n = 1-4) as a heterogeneous catalyst. Solvent-free condition, recyclability of the catalyst, very good yield and scaling up of the reactions are important attributes in this catalysis. Aromatic amines do not participate effectively in the reaction.

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Catalytic high pressure synthesis of hindered β-aminoesters

Cited by 120 publications

References 13 publications

The Hydroamination of methyl acrylates with amines over zeolites

The Hydroamination of methyl acrylates with amines over zeolites

Accelerated C–N Bond Formation in Dropcast Thin Films on Ambient Surfaces

Phosphate Impregnated Titania: An Efficient Reusable Heterogeneous Catalyst for Aza-Michael Reactions Under Solvent-Free Condition

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