Synlett 2019; 30(20): 2233-2246
DOI: 10.1055/s-0039-1690738
account
© Georg Thieme Verlag Stuttgart · New York

Breaking Carbon–Fluorine Bonds with Main Group Nucleophiles

Greg Coates
,
Feriel Rekhroukh
,
Mark R. Crimmin
Department of Chemistry, Molecular Sciences Research Hub, Imperial College London, White City, London, W12 0BZ, UK   Email: m.crimmin@imperial.ac.uk
› Author Affiliations
We are grateful to the European Research Council for support in the form of an ERCstG (Fluorofix: 677367) and Marie Curie Sponsporship (Fluorocat and Fluorocross). GC is thankful for EPSRC funding in the form of a DTP scholarship.
Further Information

Publication History

Received: 23 September 2019

Accepted after revision: 15 October 2019

Publication Date:
12 November 2019 (online)

Abstract

In this Account we describe a series of new reactions that we, and others, have reported that involve the transformation of C–F bonds into C–Mg, C–Al, C–Si, C–Fe and C–Zn bonds. We focus on the use of highly reactive main group nucleophiles and discuss aspects of reaction scope, selectivity and mechanism.

1 Introduction

1.1 The Fluorocarbon Industry and Sustainability

1.2 Production of Fluorocarbons

1.3 Properties of Fluorocarbons

1.4 Our Work

2 Results and Discussion

2.1 Low-Valent Main Group Compounds

2.1.1 Reactions with Fluoroarenes

2.1.2 Reactions with Fluoroalkanes

2.1.3 Reactions with Fluoroalkenes

2.2 Main Group Nucleophiles (M1–M2)

2.2.1 Reactions of M1–M2 Nucleophiles with Fluoroarenes

2.2.2 Reactions of M1–M2 Nucleophiles with Fluoroalkanes

2.2.3 Reactions of M1–M2 Nucleophiles with Fluoroalkenes

3 Summary and Perspective

 
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