Copper-Catalyzed Cross-Coupling of O-Alkyl Hydroxamates with Aryl Iodides

Kukosha, Tatyana; Trufilkina, Nadezhda; Belyakov, Sergey; Katkevičs, Mārtiņš

doi:10.1055/s-0031-1290384

Cited by 10 publications

References 6 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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Transition Metal‐FreeO‐Arylation ofN‐Alkoxybenzamides Enabled by Aryl(trimethoxyphenyl)iodonium Salts

et al. 2023

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Herein, we develop a metal catalyst‐free protocol for O‐arylation of benzamide hydroxamate esters. The chemoselective O‐ versus N‐arylation of the amides was tuned by varying the electronic and/or steric properties of the diaryliodonium salt and/or the substrate. The O‐arylation reaction would preferentially occur for sterically and electronically diverse substrates. This study, which reveals the possibility of substituent‐ and reagent‐controlled chemoselectivity, with diaryliodonium salts might attract interest in the area of hypervalent iodine chemistry.magnified image

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