Silver-catalyzed Radical Aminofluorination of Unactivated Alkenes in Aqueous Media

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2013 Mar 20

PMID 23506151

Citations 34

Authors

Zhaodong Li

Liyan Song

Chaozhong Li

Affiliations

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Abstract

We report herein a mild and catalytic intramolecular aminofluorination of unactivated alkenes. Thus, with the catalysis of AgNO3, the reactions of various N-arylpent-4-enamides with Selectfluor reagent in CH2Cl2/H2O led to the efficient synthesis of 5-fluoromethyl-substituted γ-lactams. A mechanism involving silver-catalyzed oxidative generation of amidyl radicals and silver-assisted fluorine atom transfer was proposed.

Citing Articles

A Catalytic Three-Component Aminofluorination of Unactivated Alkenes with Electron-Rich Amino Sources.

Dong J, Liang Y, Li Y, Guan W, Zhang Q, Fu J Adv Sci (Weinh). 2024; 11(12):e2305006.

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Cobalt-Catalyzed Aerobic Aminocyclization of Unsaturated Amides for the Synthesis of Functionalized γ- and δ-Lactams.

Freis M, Balkenhohl M, Fischer D, Georgiev T, Sarott R, Carreira E Org Lett. 2023; 25(34):6380-6384.

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Modular synthesis of unsaturated aza-heterocycles via copper catalyzed multicomponent cascade reaction.

Wei S, Zhang G, Wang Y, You M, Wang Y, Zhou L iScience. 2023; 26(3):106137.

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Silver-catalyzed cascade cyclization and functionalization of -aryl-4-pentenamides: an efficient route to γ-lactam-substituted quinone derivatives.

Fang Z, Xie L, Wang L, Zhang Q, Li D RSC Adv. 2022; 12(41):26776-26780.

PMID: 36320855 PMC: 9490777. DOI: 10.1039/d2ra05283k.