Towards Catalytic C–H Activation Using Main Group Elements

This Account is dedicated to the memory of Keith Fagnou.

Abstract

Catalytic C–H activation reactions are now established as a means to directly transform organic molecules and are commonly associated with metals such as palladium, rhodium, ruthenium and iridium. This Account will describe a short number of reports demonstrating that structures containing main group elements can facilitate C–H activation processes. In particular, boron-based catalysts can promote catalytic arene C–H borylation reactions, and an emerging approach using phosphenium ions can also cleave sp² C–H bonds. These processes use a Lewis acidic main group atom combined with a pendant base to cleave C–H bonds, which compares with metal-catalyzed reactions that proceed via concerted metalation deprotonation mechanisms.

1 Introduction

2 Metal-Catalyzed C–H Activation via CMD/AMLA Mechanisms

3 C–H Borylation via Boron-Based Catalysts

4 C–H Activation Using Phosphenium Ions

5 Conclusions

Key words

C–H activation - main group catalysis - concerted metalation–deprotonation - borylation - phosphenium ions

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