Highly efficient and practical phosphoramidite–copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles

Zhang, Zhanjin; Mao, Jincheng; Zhu, Di; Wu, Fan; Chen, Huilin; Wan, Boshun

doi:10.1016/j.tet.2006.02.062

Cited by 123 publications

(40 citation statements)

References 47 publications

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“…Column chromatography (pentane/diethyl ether 2:1) yielded 2 c (184 mg, 0.86 mmol, 86 %). Butylpyridin-2-ylamine (2 h): [24] [IrClA C H T U N G T R E N N U N G (cod)] 2 (160 mL, 0.01 mmol, 0.0625 m in THF) was combined with Py 2 NPiPr 2 (160 mL, 0.02 mmol, 0.125 m in THF) in THF instead of diglyme (200 mL). The substrates were added and the reaction was allowed to proceed for 48 h at 70 8C.…”

Section: Methodsmentioning

confidence: 99%

Selective Iridium‐Catalyzed Alkylation of (Hetero)Aromatic Amines and Diamines with Alcohols under Mild Reaction Conditions

Blank¹,

Michlik²,

Kempe³

2009

Chemistry A European J

199

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A P,N-ligand-coordinated iridium complex has been employed as an efficient catalyst for the selective monoalkylation of (hetero)aromatic amines with alcohols. A significant improvement of this alkylation method has been achieved, such that it can be performed at a temperature of 70 degrees C and with catalyst loadings as low as 0.1 mol % Ir, while still affording excellent yields of secondary amines. Furthermore, the high selectivity of this catalyst for the monoalkylation of aromatic amino functions has been successfully exploited for the alkylation of diamines in both symmetric and nonsymmetric fashions, providing a novel and very efficient synthetic tool for the preparation of N,N'-dialkylated aromatic diamines.

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Section: Methodsmentioning

confidence: 99%

Selective Iridium‐Catalyzed Alkylation of (Hetero)Aromatic Amines and Diamines with Alcohols under Mild Reaction Conditions

Blank¹,

Michlik²,

Kempe³

2009

Chemistry A European J

199

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“…Mit dieser Methode wurden auch verschiedene Aryliodide, Brompyridine und 5-Brompyrimidine mit Alkylaminen, Arylaminen und N-Heterocyclen verknüpft. [434] Die Kupplung von Heterocyclen erforderte jedoch höhere Mengen CuBr und des Phosphoramidit-Liganden L50, um gute Produktausbeuten zu erhalten.…”

Section: Phosphoramidit-ligandenunclassified

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

2010

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Die asymmetrische Katalyse mit Übergangsmetallkomplexen ist die Grundlage unzähliger stereoselektiver Umwandlungen und hat damit das Bild der modernen Synthesechemie gewandelt. Der Schlüssel zum Erfolg war die Entwicklung chiraler Liganden zur Kontrolle der Regio‐, Diastereo‐ und Enantioselektivität. Dabei haben sich Phosphoramidite als eine äußerst vielseitige und leicht zugängliche Klasse von chiralen Liganden erwiesen. Ihre modulare Struktur ermöglicht die Herstellung von Ligandenbibliotheken und erleichtert die Feinabstimmung für eine bestimmte katalytische Reaktion. Phosphoramidite bewirken oft außerordentlich hohe Stereoselektivitäten, und ihre einzähnige Natur ist in der kombinatorischen Katalyse, die gemischte Liganden verwendet, unverzichtbar. In diesem Aufsatz werden neue Entwicklungen in der asymmetrischen Katalyse mit Phosphoramiditen diskutiert, wobei der Schwerpunkt auf der Bildung von Kohlenstoff‐ Kohlenstoff‐ und Kohlenstoff‐Heteroatom‐Bindungen liegt.

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“…The spectral data were in accordance with those reported in the literature. [42] N-Benzyl-N-methylpyrimidin-5-amine (50) ( Table 6) 5-(4-Ethylpiperazin-1-yl)pyrimidine (51) ( Table 6): Following general procedure C, 153 mg of 51 (80 % yield) were isolated (R f = 0.25, 10 % methanol in ethyl acetate) as a colorless oil. The spectral data were in accordance with those reported in the literature.…”

Section: N-methyl-n-phenyl-3-aminothiophene (20) (mentioning

confidence: 99%

Pd‐Catalyzed Aryl Amination Mediated by Well Defined, N‐Heterocyclic Carbene (NHC)–Pd Precatalysts, PEPPSI

Organ

Abdel‐Hadi

Avola

et al. 2008

Chemistry A European J

228

105

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Pd-N-heterocyclic carbene (NHC)-catalyzed Buchwald-Hartwig amination protocols mediated by Pd-PEPPSI precatalysts is described. These protocols provide access to a range of hindered and functionalized drug-like aryl amines in high yield with both electron-deficient and electron-rich aryl- and heteroaryl chlorides and bromides. Variations in solvent polarity, base and temperature are tolerated, enhancing the scope and utility of this protocol. A mechanistic rationalization for base strength (pKb) requirements is also provided.

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Highly efficient and practical phosphoramidite–copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles

Cited by 123 publications

References 47 publications

Selective Iridium‐Catalyzed Alkylation of (Hetero)Aromatic Amines and Diamines with Alcohols under Mild Reaction Conditions

Selective Iridium‐Catalyzed Alkylation of (Hetero)Aromatic Amines and Diamines with Alcohols under Mild Reaction Conditions

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

Pd‐Catalyzed Aryl Amination Mediated by Well Defined, N‐Heterocyclic Carbene (NHC)–Pd Precatalysts, PEPPSI

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