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Synthesis 2009(23): 3905-3929  
DOI: 10.1055/s-0029-1217080
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Trifluoromethyl Pyrroles and Their Benzo Analogues

Vasiliy M. Muzalevskiya, Aleksey V. Shastinb, Elizabeth S. Balenkovaa, Günter Haufe*c, Valentine G. Nenajdenko*a
a Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russian Federation
e-Mail: nen@acylium.chem.msu.ru;
b Institute of Problems of Chemical Physics, Chernogolovka, Moscow Region 142432, Russian Federation
e-Mail: shastin@icp.ac.ru;
c Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
Further Information

Publication History

Received 9 June 2009
Publication Date:
26 October 2009 (online)

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Abstract

Approaches towards trifluoromethylpyrroles and their benzo analogues are reviewed.

1 Introduction

2 Synthesis of Trifluoromethylpyrroles

2.1 Direct Trifluoromethylation

2.1.1 Radical Trifluoromethylation

2.1.2 Electrophilic Trifluoromethylation

2.1.3 Nucleophilic Trifluoromethylation

2.2 Synthesis by Cycloaddition Reactions

2.2.1 [3+2] Cycloaddition

2.2.2 [4+2] Cycloaddition and Cycloreversion

2.3 Synthesis Based on Carbonyl Compounds

2.4 Synthesis Based on α,β-Unsaturated Trifluoromethyl Ketones

2.5 Synthesis Based on Toluenesulfonylmethyl Isocyanide and Isocyanoacetate

2.6 Miscellaneous Approaches

3 Synthesis of Trifluoromethylindoles

3.1 Direct Trifluoromethylation

3.2 Formation of the C3-C4 Bond

3.3 Formation of the C2-C3 Bond

3.4 Formation of the C2-N Bond

4 Synthesis of Trifluoromethylindolizines

5 Conclusions

Key words

fluorine - heterocycles - pyrroles - indoles