Silver-Mediated Perfluoroalkylation Reactions

Dedicated to Armin de Meijere on the occasion of his 75^th birthday

Abstract

Direct perfluoroalkylation reactions, especially trifluoromethylations of organic substrates, are of particular importance in modern organic chemistry as they allow rapid access to perfluoroalkylated molecules. In contrast to common metal-mediated perfluoroalkylations­, recently developed silver-mediated perfluoroalkylation protocols offer the opportunity for orthogonal introduction of fluorine containing groups in organic compounds. This review gathers recent progress on silver-mediated perfluoroalkylation reactions and gives an overview over efficient syntheses, properties, and reactivity of perfluoroorganosilver(I) compounds. In addition, cooperative effects with copper-mediated processes are discussed.

1 Introduction

2 Syntheses and Properties of Perfluoroorganosilver Compounds­

3 Silver-Mediated Perfluoroalkylations

3.1 Perfluoroorganosilver Compounds in Copper-Mediated Perfluoroalkylations

3.2 Perfluoroorganosilver Compounds as Precursors for Radicals­

3.3 Perfluoroorganosilver Compounds as Nucleophilic Reagents­

3.4 Silver-Catalyzed Perfluoroalkylations

4 Conclusion and Outlook

Key words

perfluoroalkylation - trifluoromethylation - silver - perfluoroorganyls - arenes

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