Copper-Catalyzed Ring-Opening 1,3-Aminotrifluoromethylation of Arylcyclopropanes

Huan Zhang; Haiwen Xiao; Feng Jiang; Yewen Fang; Lin Zhu; Chaozhong Li

doi:10.1021/acs.orglett.1c00390

Copper-Catalyzed Ring-Opening 1,3-Aminotrifluoromethylation of Arylcyclopropanes

Org Lett. 2021 Mar 19;23(6):2268-2272. doi: 10.1021/acs.orglett.1c00390. Epub 2021 Mar 9.

Authors

Huan Zhang¹, Haiwen Xiao², Feng Jiang², Yewen Fang³, Lin Zhu², Chaozhong Li^{1

2

3}

Affiliations

¹ School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China.
² Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
³ School of Materials and Chemical Engineering, Ningbo University of Technology, No. 201 Fenghua Road, Ningbo 315211, China.

PMID: 33689390
DOI: 10.1021/acs.orglett.1c00390

Abstract

The copper-catalyzed reaction of arylcyclopropanes, N-fluorobis(arenesulfonyl)imides, and (bpy)Zn(CF₃)₂ (bpy = 2,2'-bipyridine) at room temperature affords the corresponding ring-opening 1,3-aminotrifluoromethylation products in satisfactory yields. The protocol is highly regioselective, providing a convenient entry to γ-trifluoromethylated amines. A mechanism involving the trifluoromethylation of benzyl radicals is proposed.