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

He Zhao; Xiu Li; Min Zhang

doi:10.1039/d3ob01494k

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

Org Biomol Chem. 2023 Nov 15;21(44):8883-8887. doi: 10.1039/d3ob01494k.

Authors

He Zhao^{1

2}, Xiu Li¹, Min Zhang¹

Affiliations

¹ School of Chemistry and Chemical Engineering, South China University of Technology, Wushan Rd-381, Guangzhou 510641, People's Republic of China. minzhang@scut.edu.cn.
² Chemistry & Chemical Engineering, Yancheng Institute of Technology, Yancheng, China.

PMID: 37902574
DOI: 10.1039/d3ob01494k

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.