Recent Advances in Transition-Metal-Catalyzed Trifluoromethylation and Related Transformations

Dedicated to Professor Huilin Chen on the occasion of his 75^th birthday

Abstract

The incorporation of fluorine-containing moieties into organic compounds is of great importance in pharmaceutical, agricultural, and materials science. Transition-metal-mediated perfluoroalkylation reactions have been studied in the past few decades and, owing to need for low-cost and environmentally friendly processes in the industrial and academic communities, the catalytic reaction has attracted much attention and has become a hot research field. Herein, an overview of recent advances on transition-metal-catalyzed trifluoromethylation and difluoromethylation reactions is given. Trifluoromethylthiolation and trifluoromethoxylation reactions are also reviewed.

1 Introduction

1.1 Transition-Metal–Trifluoromethyl Complexes

1.2 Stoichiometric Trifluoromethylation

2 Transition-Metal-Catalyzed Trifluoromethylation

2.1 Copper-Catalyzed Reactions

2.2 Palladium-Catalyzed Reactions

2.3 Other Transition-Metal-Catalyzed Reactions

3 Difluoromethylation

3.1 Direct Difluoromethylation

3.2 Indirect Difluoromethylation

4 Trifluoromethylthiolation

5 Trifluoromethoxylation

6 Conclusion

Key words

transition-metal-catalyzed - trifluoromethylation - difluoromethylation - trifluoromethylthiolation - trifluoromethoxylation

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