Electrophilic amination of higher order cuprates with N,O-bis(trimethylsilyl)hydroxylamine

Casarini, Antonella; Dembech, P.; Lazzari, Dario; Marini, Elisabetta; Reginato, Gianna; Ricci, Alfredo; Seconi, Giancarlo

doi:10.1021/jo00073a018

Cited by 81 publications

(26 citation statements)

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“…Electrophilic amination of dialkylcuprates with 22a-c was presumed to be an S N 2 process in which the aminating reagent interacted with the dimeric cuprate to form an intermediate and a mechanism very similar to that proposed for the electrophilic amination of 20 with diarylcyanocuprates 114 was suggested.…”

Section: Scheme 37bmentioning

confidence: 99%

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Synthesis of amines by the electrophilic amination of organomagnesium, -zinc, -copper, and -lithium reagents

Daşkapan

2011

Arkivoc

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Section: Scheme 37bmentioning

confidence: 99%

“…114 According to the proposed mechanism of Ricci et. al., in the first step of the amination reaction, one of the R groups in R 2 CuCNLi 2 abstracts one proton from the aminating reagent to give a lower-order cyanocuprate and lithium N-silyl-N-siloxamide (nitrenoid), 21a.…”

Section: Scheme 33mentioning

confidence: 99%

Synthesis of amines by the electrophilic amination of organomagnesium, -zinc, -copper, and -lithium reagents

Daşkapan

2011

Arkivoc

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“…[183] Die Reaktion des Benzoesäureethylesterderivats 213 mit 2 (0 8C, 1 h), gefolgt von der Zugabe von CuCl·2 LiCl, liefert eine Organokupferspezies, die nachfolgend mit lithiiertem Morpholin zu dem intermediären Lithium-Amidocuprat 214 reagiert. Dieses Reagens geht in Gegenwart von Chloranil (201; 1.2 ¾quiv., À50 8C, 12 h) eine oxidative Aminierung [184][185][186] zu dem tertiären aromatischen Amin 215 ein (70 % Ausbeute; Schema 40). [168] Vielfältige Heterocyclen werden durch dieses Verfahren oxidativ aminiert.…”

Section: Tmpmgcl·licl Und Verwandte Magnesiumbasenunclassified

Regio‐ und chemoselektive Metallierung von Arenen und Heteroarenen mit gehinderten Metallamidbasen

et al. 2011

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Die Synthese hoch funktionalisierter Organometallverbindungen gelingt durch C‐H‐Aktivierung zahlreicher ungesättigter Substrate mit Lithiumchlorid‐solubilisierten 2,2,6,6‐Tetramethylpiperidyl‐Basen (TMPnMXm⋅p LiCl). Diese Reagentien erweisen sich als exzellent zur Umwandlung vielfältiger aromatischer sowie heterocyclischer Substrate in nützliche metallorganische Reagentien mit weiter Anwendungsbreite in der organischen Synthese.

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“…Although electrophilic amination is another method to prepare primary amines, it has been rarely employed in organic synthesis [6]. As mentioned in the above S N 2-type reaction, oxime derivatives were found to behave as electrophilic amination reagents.…”

Section: Preparation Of Primary Amines From O-sulfonyloximes and Grigmentioning

confidence: 99%

Synthesis of azaheterocycles from oxime derivatives

Narasaka

2003

Pure and Applied Chemistry

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Electrophilic amination of Grignard reagents has been accomplished by using O-sulfonyloximes as amination reagents. Benzophenone O-sulfonyloxime derivatives react with Grignard reagents on sp 2 nitrogen, yielding primary amines by successive hydrolysis of the resulting N-alkylimines.Various cyclic imines are synthesized by Pd-catalyzed reaction from olefinic oxime derivatives. That is, treatment of O-pentafluorobenzoyloximes of olefinic ketones with a catalytic amount of Pd(PPh 3 ) 4 and triethylamine affords nitrogen-containing heterocycles, such as pyrroles, pyridines, isoquinolines, spiro-imines, and aza-azulenes. This reaction proceeds via the initial formation of alkylideneaminopalladium(II) species generated by oxidative addition of the oximes to the Pd(0) complex, and the following intramolecular amination on the olefinic moiety.Cyclic imines are prepared from γ,δ-unsaturated O-acetyloximes by treatment with acetic acid and 1,4-cyclohexadiene in the presence of a catalytic amount of 1,5-naphthalenediol. γ,δ-Unsaturated ketone O-methoxycarbonyloximes are transformed to 2-bromomethyl-3,4-dihydro-2H-pyrroles by the action of a catalytic amount of Cu(I) bromide dimethyl sulfide complex and lithium bromide.

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Electrophilic amination of higher order cuprates with N,O-bis(trimethylsilyl)hydroxylamine

Cited by 81 publications

References 0 publications

Synthesis of amines by the electrophilic amination of organomagnesium, -zinc, -copper, and -lithium reagents

Synthesis of amines by the electrophilic amination of organomagnesium, -zinc, -copper, and -lithium reagents

Regio‐ und chemoselektive Metallierung von Arenen und Heteroarenen mit gehinderten Metallamidbasen

Synthesis of azaheterocycles from oxime derivatives

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