Highly efficient copper-catalyzed N-arylation of alkylamines with aryl iodides using phosphoramidite as ligand

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

doi:10.1016/j.catcom.2005.07.016

Cited by 19 publications

(2 citation statements)

References 38 publications

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“…Pyridin-3-amine, and pyrimidin-2-amine heteroarylamines gave the expected diphenylamine, N -phenylpyridin-3-amine, and N -phenylpyrimidin-2-amine with good conversion (entries 11 and 12, Table 2). Such a result shows a similar yield albeit with shorter reaction time (24 h–40 h), compared with known literature [25,26,27,28]. …”

Section: Resultssupporting

confidence: 84%

Highly Efficient and Reusable Copper-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides

et al. 2009

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Section: Resultssupporting

confidence: 84%

Highly Efficient and Reusable Copper-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides

et al. 2009

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“…Phosphoramidite ligands have also been used in the copper-catalyzed arylation of aryl halides 318 with a variety of cyclic and acyclic amines 319 (Scheme 100). [433] The coupling products 320 were usually obtained in very good yields by using racemic biphenol-based phosphoramidite ligand L50. This method was extended to the coupling of several aryl iodides, bromopyridines, and 5-bromopyrimidine with alkyl amines, aryl amines, and N heterocycles.…”

Section: Copper-catalyzed N-arylation and Related Reactionsmentioning

confidence: 99%

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Teichert¹,

Feringa²

2010

Angew Chem Int Ed

638

340

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Asymmetric catalysis with transition-metal complexes is the basis for a vast array of stereoselective transformations and has changed the face of modern synthetic chemistry. Key to this success has been the design of chiral ligands to control the regio-, diastereo-, and enantioselectivity. Phosphoramidites have emerged as a highly versatile and readily accessible class of chiral ligands. Their modular structure enables the formation of ligand libraries and easy fine-tuning for a specific catalytic reaction. Phosphoramidites frequently show exceptional levels of stereocontrol, and their monodentate nature is essential in combinatorial catalysis, where a ligand-mixture approach is used. In this Review, recent developments in asymmetric catalysis with phosphoramidites used as ligands are discussed, with a focus on the formation of carbon-carbon and carbon-heteroatom bonds.

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Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

2014

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The copper‐catalyzed arylation and vinylation of nitrogen nucleophiles is a highly versatile method for the construction of sp 2 C–N bonds. Copper‐catalyzed C–N bond formation has an extensive history and the field has been reinvigorated with the development of ligand‐promoted catalyst systems that provide general and effective reactions under relatively mild conditions. Copper promotes arylation and vinylation of a wide range of nitrogen nucleophiles, including amines, nitrogen heterocycles, and amide derivatives. The reactivity profile is complementary to that of palladium and often offers orthogonal chemoselectivity. This chapter presents a thorough overview of the copper‐catalyzed coupling of aryl and vinyl halides with nitrogen nucleophiles. Current understanding of the mechanism of this process is presented along with a detailed overview of the scope and limitations of this reaction along with optimal reaction conditions for the coupling of various nitrogen nucleophile classes.

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Highly efficient copper-catalyzed N-arylation of alkylamines with aryl iodides using phosphoramidite as ligand

Cited by 19 publications

References 38 publications

Highly Efficient and Reusable Copper-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides

Highly Efficient and Reusable Copper-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

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