Synlett 2013; 24(15): 1887-1898
DOI: 10.1055/s-0033-1339435
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© Georg Thieme Verlag Stuttgart · New York

Organometallic Aspects of Fluoroalkylation Reactions with Copper and Nickel

Huan Wang
Department of Chemistry, Lehigh University, 6 E. Packer Avenue, Bethlehem PA 18015, USA   Fax: +1(610)7586536   Email: dav512@lehigh.edu
,
David A. Vicic*
Department of Chemistry, Lehigh University, 6 E. Packer Avenue, Bethlehem PA 18015, USA   Fax: +1(610)7586536   Email: dav512@lehigh.edu
› Author Affiliations
Further Information

Publication History

Received: 22 May 2013

Accepted after revision: 19 June 2013

Publication Date:
22 August 2013 (online)


Abstract

The development of perfluoroalkylation methods has become increasingly important in synthetic chemistry. However, many of the metal-mediated transformations that occur readily with alkyl substrates can proceed slowly, with limited scope, or not proceed at all with fluoroalkyl derivatives. To develop more sophisticated transformations with fluoroalkyl groups using base metals, a better understanding of their fundamental fluoro-organometallic chemistry is needed.

This account describes our recent investigations into the organometallic chemistry of well-defined nickel– and copper–fluoroalkyl complexes, as well as our efforts towards trifluoromethoxylations and trifluoromethylthiolations using those metals. Synthetic routes to the new complexes are discussed, as are their structural and electrochemical properties and chemical reactivities.

1 Introduction

2 Bottling a Copper(I)–Trifluoromethyl Source

3 The Redox Chemistry of Copper– and Nickel–Fluoroalkyl Complexes

4 Nickel- and Copper-Mediated Trifluoromethylthiolations

5 The Organometallic Chemistry of Nickel–Perfluoroalkyl Complexes

6 Outlook

 
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