Back to Search Start Over

Electrochemical Trifluoromethylation of Glycals.

Authors :
Liu M
Luo ZX
Li T
Xiong DC
Ye XS
Source :
The Journal of organic chemistry [J Org Chem] 2021 Nov 19; Vol. 86 (22), pp. 16187-16194. Date of Electronic Publication: 2021 Aug 26.
Publication Year :
2021

Abstract

Carbohydrates play essential roles in various physiological and pathological processes. Trifluoromethylated compounds have wide applications in the field of medicinal chemistry. Herein, we report a practical and efficient trifluoromethylation of glycals by an electrochemical approach using CF <subscript>3</subscript> SO <subscript>2</subscript> Na as the trifluoromethyl source and MnBr <subscript>2</subscript> as the redox mediator. A variety of trifluoromethylated glycals bearing different protective groups are obtained in 60-90% yields with high regioselectivity. The successful capture of a CF <subscript>3</subscript> radical indicates that a radical mechanism is involved in this reaction.

Subjects

Subjects :
Oxidation-Reduction

Details

Language :
English
ISSN :
1520-6904
Volume :
86
Issue :
22
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
34435785
Full Text :
https://doi.org/10.1021/acs.joc.1c01318