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Synthesis 2011(16): 2505-2529  
DOI: 10.1055/s-0030-1260088
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Fluorinated Thiophenes and Their Analogues

Olga V. Serdyuk*a, Vladimir T. Abaevb, Alexander V. Butinc, Valentine G. Nenajdenko*d
a Southern Federal University, Department of Chemistry, Zorge 7, Rostov-on-Don 344090, Russian Federation
Fax: +7(863)2975146; e-Mail: oserduke@mail.ru;
b North-Ossetian State University, Vatutina 46, Vladikavkaz 362025, Russian Federation
c Kuban State Technological University, Moskovskaya st. 2, Krasnodar 350072, Russian Federation
d Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russian Federation
e-Mail: nen@acylium.chem.msu.ru;
Further Information

Publication History

Received 9 February 2011
Publication Date:
28 June 2011 (online)

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Abstract

Approaches towards fluorothiophenes, perfluoroalkyl­thiophenes, perfluoroarylthiophenes and their benzo-analogues are reviewed. The literature up to 2010 is highlighted.

1 Introduction

2 Synthesis of Fluorothiophenes

2.1 Functionalization of the Thiophene Ring

2.2 Heterocyclization

3 Synthesis of Perfluoroalkylthiophenes

3.1 Functionalization of the Thiophene Ring

3.2 Heterocyclization and Cycloaddition

4 Synthesis of Fluorobenzothiophenes

5 Synthesis of Perfluoroalkylbenzothiophenes

6 Synthesis of Perfluoroarylthiophenes

6.1 Organometallic Synthesis

6.2 Cross-Coupling

6.3 Heterocyclization

7 Synthesis of Perfluoroarylbenzothiophenes

8 Synthesis of Benzothiophenes with a Perfluorinated Carbocycle

9 Conclusions

Key words

fluorine - trifluoromethyl - perfluoroalkyl - perfluoro­aryl - thiophene - benzo[b]thiophene