Issue 24, 2023

Metallaphotoredox catalysis enables facile (trifluoromethyl)thiolation of alkenyl iodides

Abstract

The trifluoromethylthioether (SCF3) moiety represents a privileged functionality in pharmaceuticals and agrochemistry, however the synthesis and application of alkenyl-SCF3 compounds remain comparatively nascent. Herein, we demonstrate a nickel (Ni)-catalyzed, photoredox-based approach for the trifluoromethylthiolation of alkenyl iodides to access diverse and biologically relevant alkenyl-SCF3 compounds under mild and air-tolerant conditions. The developed methodology tolerates a broad range of substituted (hetero)aromatic and aliphatic alkenyl iodides, exhibiting general Z selectivity arising from an in situ photoisomerization mechanism. This process was readily extended to a generalized thiolation protocol through the utilization of diverse, medicinally relevant thiols to provide unique alkenyl sulfide products. The utility of the products was demonstrated by post-functionalization, providing enhanced degrees of molecular complexity in the products.

Graphical abstract: Metallaphotoredox catalysis enables facile (trifluoromethyl)thiolation of alkenyl iodides

Supplementary files

Article information

Article type
Paper
Submitted
06 Oct 2023
Accepted
03 Nov 2023
First published
03 Nov 2023

Catal. Sci. Technol., 2023,13, 7059-7067

Metallaphotoredox catalysis enables facile (trifluoromethyl)thiolation of alkenyl iodides

E. R. King, M. Tarrago and A. Ghosh, Catal. Sci. Technol., 2023, 13, 7059 DOI: 10.1039/D3CY01394D

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