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Synlett 2009(14): 2205-2216  
DOI: 10.1055/s-0029-1217554
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Fluorinated Arenes and Hetarenes Based on One-Pot Cyclizations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes

Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
b Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
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Publikationsverlauf

Received 3 February 2009
Publikationsdatum:
10. Juli 2009 (online)

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Abstract

One-pot cyclizations of fluorinated 1,3-bis(silyloxy)-1,3-butadienes and 3-alkoxy- and 3-silyloxy-2-en-1-ones provide a convenient access to various fluoro-, trifluoromethyl- and perfluoroalkyl-substituted arenes and hetarenes.

1 Introduction

2 [3+3]-Type Cyclizations of Fluorinated Enones

3 [3+3]-Type Cyclizations of Trifluoromethyl-Substituted Enones

4 [3+3]-Type Cyclizations of Perfluoroalkyl-Substituted Enones

5 [3+2]-Type Cyclizations of Fluorinated 1,3-Bis(silyloxy)-1,3-butadienes

6 [4+2]-Type Cyclizations of Fluorinated 1,3-Bis(silyloxy)-1,3-butadienes

7 Summary

Key words

arenes - heterocycles - cyclizations - organofluorine compounds - silyl enol ethers

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78

Farooq, I.; Langer, P. unpublished results.