Recent Advances in Transition-Metal-Catalyzed Silylations of Arenes with Hydrosilanes: C–X Bond Cleavage or C–H Bond Activation­ Synchronized with Si–H Bond Activation

Dedicated to Professor Xue-Long Hou on the occasion of his 60^th birthday

Abstract

Arylsilanes are valuable organosilicon compounds and attract significant research interest due to their promising applications in organic synthesis. The development of aromatic C–Si cross-coupling reactions represents a major challenge in both organosilicon chemistry and organic synthesis. A number of investigations are focused on developing transition-metal-catalyzed Si–C coupling reactions due to the associated high atom economy and superior functional group compatibility. This review describes recent advances in transition-metal-catalyzed selective silylations of aryl C–H and C–X (X = halide) bonds with hydrosilanes.

1 Introduction

2 Silylation of Arenes with Hydrosilanes via Aryl C–H Bond Activation

2.1 Rhodium-Catalyzed Dehydrogenative Silylations

2.2 Iridium-Catalyzed Dehydrogenative Silylations

2.3 Ruthenium-Catalyzed Dehydrogenative Silylations

2.4 Platinum-Catalyzed Dehydrogenative Silylations

2.5 Other Transition-Metal-Catalyzed Dehydrogenative Silylations

3 Silylation of Arenes with Hydrosilanes via Aryl C–X Bond Cleavage

3.1 Palladium-Catalyzed Silylations of Aryl Halides

3.2 Rhodium-Catalyzed Silylations of Aryl Halides

3.3 Platinum-Catalyzed Silylations of Aryl Halides

4 Conclusion

Key words

arylsilanes - transition metal - silylation - homogeneous catalysis - cross-coupling

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