Synthesis 2013; 45(21): 2919-2939
DOI: 10.1055/s-0033-1339677
review
© Georg Thieme Verlag Stuttgart · New York

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

Pinhong Chen
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: gliu@mail.sioc.ac.cn
,
Guosheng Liu*
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: gliu@mail.sioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 29 May 2013

Accepted after revision: 03 July 2013

Publication Date:
02 October 2013 (online)


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