C(sp3)-H Aerobic Alkenylation of Tetrahydroisoquinolines via Organic Electrosynthesis

Zeng He; Hui-Lin Liu; Zhen-Hua Wang; Ke-Jing Jiao; Zi-Meng Li; Zhang-Jian Li; Ping Fang; Tian-Sheng Mei

doi:10.1021/acs.joc.3c00223

C(sp³)-H Aerobic Alkenylation of Tetrahydroisoquinolines via Organic Electrosynthesis

J Org Chem. 2023 May 5;88(9):6203-6208. doi: 10.1021/acs.joc.3c00223. Epub 2023 Apr 14.

Authors

Zeng He^{1

2}, Hui-Lin Liu², Zhen-Hua Wang², Ke-Jing Jiao², Zi-Meng Li², Zhang-Jian Li^{1

2}, Ping Fang², Tian-Sheng Mei

Affiliations

¹ College of Chemistry and Materials, Sichuan Normal University, Chengdu 610068, China.
² State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

PMID: 37058587
DOI: 10.1021/acs.joc.3c00223

Abstract

A method for the C(sp³)-H alkenylation of N-aryl-tetrahydroisoquinoline (THIQ) has been developed by the combination of electrooxidation and a copper catalyst. The corresponding products were obtained with good to excellent yields under mild conditions. Besides, the addition of TEMPO as an electron mediator is crucial to this transformation, since the oxidative reaction could proceed under a low electrode potential. In addition, the catalytic asymmetric variant has also been demonstrated with good enantioselectivity.