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Synthesis 2010(11): 1804-1821  
DOI: 10.1055/s-0029-1218742
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Carbon-Fluorine Bond Formation for the Synthesis of Aryl Fluorides

Takeru Furuya, Johannes E. M. N. Klein, Tobias Ritter*
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA
Fax: +1(617)4964591; e-Mail: ritter@chemistry.harvard.edu;
Further Information

Publication History

Received 26 February 2010
Publication Date:
15 April 2010 (online)

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Abstract

A selection of carbon-fluorine bond-forming reactions is presented with particular focus on transition-metal-mediated fluorination. A brief summary of conventional fluorination reactions is followed by a discussion of fluorination reactions mediated by palladium and silver. Investigations into the mechanism as well as the conceptual difficulty associated with transition-metal-mediated carbon-fluorine bond formation are presented.

1 Introduction

2 Nucleophilic Fluorination

3 Electrophilic Fluorination

4 Balz-Schiemann Reaction

5 Palladium-Mediated C-X Bond Formation

6 Palladium-Mediated Nucleophilic Fluorination

7 Palladium-Mediated Directed Electrophilic Fluorination

8 Palladium-Mediated Electrophilic Fluorination

9 Silver-Mediated Fluorination

10 Conclusion

Key words

carbon-fluorine bond formation - transition metals - palladium - silver - catalysis

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Tang, P.; Furuya, T.; Ritter, T., submitted for publication.