Stereoselective migratory heteroaryltrifluoromethylation of allylic amines via electrosynthesis

An electrochemically initiated heteroaryltrifluoromethylation of allylic amines was developed. The cascade reaction involved the anodic oxidation of Langlois reagent (CF 3 SO 2 Na) to generate CF 3 radicals, followed by radical addition to the inactivated alkene, Smiles-type heteroaryl migration, an...

Full description

Saved in:
Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2022-08, Vol.24 (16), p.6138-6144
Main Authors: Lan, Jianyong, Lin, Kejun, Zhang, Xing, Zhu, Tingshun
Format: Article
Language:English
Subjects:
Amines
Anodizing
Bioactive compounds
Biological activity
Cascade chemical reactions
Free radicals
Green chemistry
Nitrogen radicals
Oxidation
Reagents
Reducing agents
Regioselectivity
Stereoselectivity
Sulfur dioxide
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An electrochemically initiated heteroaryltrifluoromethylation of allylic amines was developed. The cascade reaction involved the anodic oxidation of Langlois reagent (CF 3 SO 2 Na) to generate CF 3 radicals, followed by radical addition to the inactivated alkene, Smiles-type heteroaryl migration, and the reduction of nitrogen radicals. Unlike the conventional oxidative reaction mode, the SO 2 molecules from the Langlois reagent and Smiles rearrangement probably served as chemical reductants in the reaction cascade, giving a redox-neutral electrosynthesis. The reaction exhibited excellent regioselectivity and stereoselectivity. It provides an efficient method for the synthesis of enantiomerically pure β-heteroaryl-γ-trifluoromethyl amines and the stereoselective late-stage modification of biologically active compounds.
ISSN:1463-9262
1463-9270
DOI:10.1039/D2GC00960A