S -Trifluoromethyl thioesters as bifunctional reagents for acyl-trifluoromethylthiolation of alkenes and 1,3-enynes via photoredox/copper dual catalysis

The difunctionalization of unsaturated compounds offers great advantages regarding step- and atom-economy for the construction of various vicinal functional groups. Introducing acyl and trifluoromethylthio groups into compounds simultaneously still remains a challenge. Using S -trifluoromethyl thioe...

Full description

Saved in:
Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2023-04, Vol.25 (7), p.2723-2729
Main Authors: Zhang, Zhong, Tian, Yang, Li, Xiaowei, Wang, Zemin, Liu, Ruihua, Chen, Ping, Li, Xiangqian, Dai, Jiajia, Shi, Dayong
Format: Article
Language:English
Subjects:
Alkenes
Atom economy
Catalysis
Copper
Functional groups
Green chemistry
Ketones
Reagents
Thioesters
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:The difunctionalization of unsaturated compounds offers great advantages regarding step- and atom-economy for the construction of various vicinal functional groups. Introducing acyl and trifluoromethylthio groups into compounds simultaneously still remains a challenge. Using S -trifluoromethyl thioesters as bifunctional reagents, we developed photoredox/copper dual-catalyzed 1,2-acyl-trifluoromethylthiolation of alkenes and 1,4-acyl-trifluoromethylthiolation of 1,3-enynes. β-Trifluoromethylthiolated ketones and δ-trifluoromethylthiolated β-allenyl ketones can be obtained in moderate to good yields with broad functional group compatibility. More broadly, by combining S-trifluoromethyl thioesters with other radical precursors, trifluoromethylthio-fluoroalkylation and trifluoromethylthio-arylation of alkenes could be realized, respectively.
ISSN:1463-9262
1463-9270
DOI:10.1039/D3GC00266G