Breaking Carbon–Fluorine Bonds with Main Group Nucleophiles

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

Key words

fluorine - fluorocarbons - main group - reaction mechanisms - C–F bond activation

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