Nickel-catalysed couplings of aryl chlorides with secondary amines and piperazines

Brenner, Éric; Schneider, Raphaël; Fort, Yves

doi:10.1016/s0040-4020(99)00788-7

Cited by 101 publications

(33 citation statements)

References 61 publications

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“…Reduction and homocoupling byproducts were typically observed, but their levels could be reduced using higher levels of Ni catalyst. Further optimization of this system reduced the catalyst loading to 20% and broadened the amination scope to acyclic secondary amines 381. However the reaction was sensitive to the nature of the substrates and the electronic effects of the substituents.…”

Section: Nickel-catalyzed Reactions Of Aryl and Vinyl Sulfonates Amentioning

confidence: 99%

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

et al. 2010

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Section: Nickel-catalyzed Reactions Of Aryl and Vinyl Sulfonates Amentioning

confidence: 99%

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

et al. 2010

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“…The spectral data were in accordance with those reported in literature. [37] N-Methyldiphenylamine (25) ( Table 3): Following general procedure A (RT), 139 mg of 25 (76 % yield) were isolated (R f = 0.3, 5 % Et 2 O in pentane) as a white, crystalline solid. The spectral data were in accordance with those reported in literature.…”

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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“…In 1998, Brenner and Fort developed a mild catalytic procedure for the coupling of aryl chlorides with secondary amines or piperazines 21a. The reactions proceeded in two steps.…”

Section: Development Of Nickel‐catalyzed Aminationmentioning

confidence: 99%

Ni‐Catalyzed Amination Reactions: An Overview

Marín

Rama

Nicasio

2016

The Chemical Record

130

106

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Nitrogen-containing organic compounds are valuable in many fields of science and industry. The most reliable method for the construction of C(sp(2) )-N bonds is undoubtedly palladium-catalyzed amination. In spite of the great achievements made in this area, the use of expensive Pd-based catalysts constitutes an important limitation for large-scale applications. Since nickel is the least expensive and most abundant among the group 10 metals, the interest in Ni-based catalysts for processes typically catalyzed by palladium has grown considerably over the last few years. Herein, we revise the development of Ni-catalyzed amination reactions, emphasizing the most relevant and recent advances in the field.

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Nickel-catalysed couplings of aryl chlorides with secondary amines and piperazines

Cited by 101 publications

References 61 publications

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

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

Ni‐Catalyzed Amination Reactions: An Overview

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