Nickel-catalyzed displacement reactions of aryl halides

Cramer, Richard D.; Coulson, D. R.

doi:10.1021/jo00904a001

Cited by 97 publications

(36 citation statements)

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“…Nickel complexes were also the first ones to be reported to promote this reaction which was actually disclosed before the reverse process. Indeed, Cramer and Coulson reported in the mid-1970s that bromobenzene 9 Br could be transformed to chlorobenzene 9 Cl upon reaction with a catalytic amount of nickel(II) chloride in the presence of lithium chloride in DMF at 210°C for 6 h (Figure 8 , top; Cramer and Coulson, 1975 ).…”

Section: Halogen Exchange In Aryl Halidesmentioning

confidence: 99%

Metal-Mediated Halogen Exchange in Aryl and Vinyl Halides: A Review

et al. 2018

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Halogenated arenes and alkenes are of prime importance in many areas of science, especially in the pharmaceutical, agrochemical, and chemical industries. While the simplest ones are commercially available, some of them are still hardly accessible depending on their substitution patterns and the nature of the halogen atom. Reactions enabling the selective and efficient replacement of the halogen atom of an aryl or alkenyl halide by another one, lighter, or heavier, are therefore of major importance since they can be used for example to turn a less reactive aryl/alkenyl chloride into the more reactive iodinated derivatives or, in a reversed sense, to block an undesired reactivity, for late-stage modifications or for the introduction of a radionuclide. If some halogen exchange reactions are possible with activated substrates, they usually require catalysis with metal complexes. Remarkably efficient processes have been developed for metal-mediated halogen exchange in aryl and vinyl halides: they are overviewed, in a comprehensive manner, in this review article.

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Section: Halogen Exchange In Aryl Halidesmentioning

confidence: 99%

Metal-Mediated Halogen Exchange in Aryl and Vinyl Halides: A Review

et al. 2018

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“…Fifteen years later, Cramer and Coulson reported a comprehensive study of the effect of the variation in the reaction conditions and catalyst composition for the nickel‐catalyzed amination reaction 18. Interestingly, they found that Ni(0) complexes, such as [Ni(CO) 2 (dppe)] and [Ni(CO) 2 (PPh 3 ) 2 ] (dppe = 1,2‐bis(diphenylphosphino)ethane, were almost as effective as NiBr 2 when used as catalysts in the amination of piperidine with bromobenzene.…”

Section: Early Stage Of Nickel‐catalyzed Aminationmentioning

confidence: 99%

Ni‐Catalyzed Amination Reactions: An Overview

Marín

Rama

Nicasio

2016

The Chemical Record

131

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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“…For related literature, see : Brandsma et al (1998); Semmelhack et al (1971); Soolinger et al (1990); Chen & Yang (2007); Cramer & Coulson (1975); Morrell & Kochi (1975); Parshall (1974); Semmelhack & Ryono (1975); Tsou & Kochi (1979a,b).…”

Section: Related Literaturementioning

confidence: 99%

trans-(4-Acetylnaphthyl)chloridobis(triphenylphosphine-κP)nickel(II) dichloromethane solvate

2008

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Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.011 Å; R factor = 0.080; wR factor = 0.183; data-to-parameter ratio = 15.0.The title compound, [Ni(C 12 H 9 O)Cl(C 18 H 15 P) 2 ]ÁCH 2 Cl 2 , was synthesized from the reaction between 1-acetyl-4-chloronaphthalene, NiCl 2 Á6H 2 O and triphenylphosphine (PPh 3 ) in ethanol. The compound contains one crystallographically unique nickel ion in a pseudo-square-planar geometry. Related literature

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Nickel-catalyzed displacement reactions of aryl halides

Cited by 97 publications

References 1 publication

Metal-Mediated Halogen Exchange in Aryl and Vinyl Halides: A Review

Metal-Mediated Halogen Exchange in Aryl and Vinyl Halides: A Review

Ni‐Catalyzed Amination Reactions: An Overview

trans-(4-Acetylnaphthyl)chloridobis(triphenylphosphine-κP)nickel(II) dichloromethane solvate

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