Issue 44, 2023

Nickel-catalyzed mild synthesis of functional γ-amino butyric acid esters via direct α-C(sp3)–H allylation of N-alkyl anilines with allyl sulfones

Abstract

Herein, by employing a readily available Ni(OAc)2·4H2O/TBHP catalyst system, we present a new method for mild synthesis of α-methylene-γ-amino butyric acid esters via direct α-C(sp3)–H allylation of N-alkyl anilines with allyl sulfones under oxidative nickel catalysis. The synthetic protocol proceeds with good substrate and functional group compatibility, operational simplicity, the use of base metal catalysts and easily accessible feedstocks, and no need for pre-functionalization of the α-site of N-alkyl anilines. In addition, the obtained products are applicable for further elaboration of functional molecules.

Graphical abstract: Nickel-catalyzed mild synthesis of functional γ-amino butyric acid esters via direct α-C(sp3)–H allylation of N-alkyl anilines with allyl sulfones

Supplementary files

Article information

Article type
Paper
Submitted
17 Sep 2023
Accepted
23 Oct 2023
First published
24 Oct 2023

Org. Biomol. Chem., 2023,21, 8883-8887

Nickel-catalyzed mild synthesis of functional γ-amino butyric acid esters via direct α-C(sp3)–H allylation of N-alkyl anilines with allyl sulfones

H. Zhao, X. Li and M. Zhang, Org. Biomol. Chem., 2023, 21, 8883 DOI: 10.1039/D3OB01494K

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