Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

Abstract

The trifluoromethylthio (SCF₃) and trifluoromethylselanyl (SeCF₃) groups possess high electron-withdrawing ability, excellent lipophilicity, good stability, and bioavailability, and they are promising structural motifs in drug design and development. Photoredox catalysis has clear benefits; it is a mild and sustainable methodology for the modification of chemical structures that enables a variety of chemical reactions that are unattainable using classical ionic chemistry. This review focuses on light-initiated trifluoromethylthiolation and trifluoromethylselenolation reactions with diverse SCF₃ and SeCF₃ reagents. Representative transformations either using photocatalysts or through EDA complexes, as well as possible reaction mechanisms, are all discussed in this article.

1 Introduction

2 Photocatalyzed Trifluoromethylthiolation

2.1 Photocatalyzed Trifluoromethylthiolation with MSCF₃ (M = H, [Me₄N], Ag)

2.2 Photocatalyzed Trifluoromethylthiolation with XSCF₃ (X = Cl, CF₃S)

2.3 Photocatalyzed Trifluoromethylthiolation with ArSO₂SCF₃

2.4 Photocatalyzed Trifluoromethylthiolation with N–SCF₃ Reagents

2.5 Photocatalyzed Trifluoromethylthiolation with Other Reagents

3 Photocatalyzed Trifluoromethylselenolation

3.1 Photocatalyzed Trifluoromethylselenolation with [Me₄N][SeCF₃]

3.2 Photocatalyzed Trifluoromethylselenolation with ArSO₂SeCF₃

4 Summary

Key words

trifluoromethylthiolation - trifluoromethylselenolation - visible-light irradiation - photoredox catalysis - radical - photocatalysis

Publication History

Received: 26 April 2024

Accepted after revision: 29 May 2024

Accepted Manuscript online:
29 May 2024

Article published online:
18 June 2024

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