Copper(I)-catalyzed intramolecular C-N coupling reactions toward 1-cyanobenzoimidazoles

Zhang, Hu; Li, Sidong; Hong, Peng-zhi; Wu, Zhanxia

doi:10.3998/ark.5550190.0012.b13

Cited by 9 publications

References 16 publications

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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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Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

2014

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The synthesis ofN‐containing heterocyclic compounds catalyzed by copper/L‐proline

2020

Applied Organom Chemis

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N‐containing heterocyclic compounds are one of the most important motifs prevalent in various bioactive natural products and pharmaceuticals. Given the significance of N‐containing heterocyclic compounds, various synthetic strategies have been developed. Copper/ligand (abbreviated as [CuL])‐catalyzed cascade reaction is a powerful and efficient tool for the construction of N‐containing heterocyclic compounds. L‐proline is one universal ligand and has been utilized in the copper‐catalyzed reactions. In this review, copper/L‐proline‐catalyzed tandem reaction to synthesize the five‐ and six‐membered compounds is emphatically introduced. By comparing the yields in the presence and absence of the ligand, the importance of L‐proline is recorded. Moreover, the function of L‐proline is expounded on the basis of the reaction mechanism from original article.

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Synthesis and biological evaluation of 1-cyano-2-amino-benzimidazole derivatives as a novel class of antitumor agents

Zhang

et al. 2013

Med Chem Res

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Copper(I)-catalyzed intramolecular C-N coupling reactions toward 1-cyanobenzoimidazoles

Abstract: Employing a CuI/2,2'-biimidazole catalyst system, the intramolecular C-N coupling reactions of various substituted aryl guanidines could be successfully carried out under mild conditions. A variety of 1-cyanobenzimidazoles were synthesized in good to excellent yields.

Cited by 9 publications

References 16 publications

Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

The synthesis ofN‐containing heterocyclic compounds catalyzed by copper/L‐proline

Synthesis and biological evaluation of 1-cyano-2-amino-benzimidazole derivatives as a novel class of antitumor agents

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