Issue 7, 2023

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
24 Jan 2023
Accepted
02 Mar 2023
First published
03 Mar 2023

Green Chem., 2023,25, 2723-2729

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

Z. Zhang, Y. Tian, X. Li, Z. Wang, R. Liu, P. Chen, X. Li, J. Dai and D. Shi, Green Chem., 2023, 25, 2723 DOI: 10.1039/D3GC00266G

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