Synthesis
DOI: 10.1055/a-2335-8627
short review

Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

Fei Li
,
Jia-Wei Song
,
Xue Han
,
We thank Wuhan University of Technology and the Natural Science Foundation of Shandong Province (China) (ZR2021MB138) for financial support.


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



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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