Nanogold(0)-Catalyzed Addition of Heteroelement σ Linkages to Functional Groups

Abstract

In recent years, supported Au nanoparticles and nanoporous Au materials have shown remarkable catalytic activity in the activation of σ heteroelement linkages such as, Si–H, Si–Si, B–B and B–Si, and their subsequent addition to functional groups, primarily π bonds. In this review article we discuss the reaction modes known to date, and attempt to discuss the mechanistic clues of these transformations which are rather unexpected in terms of conventional transition-metal catalysis concepts, given that the catalytic sites are metallic Au(0).

1 Introduction

2 Activation of Hydrosilanes

2.1 Reactions of Hydrosilanes with Alkynes

2.1.1 Hydrosilylation

2.1.2 Dehydrogenative Coupling

2.2 Reactions of Hydrosilanes with Allenes

2.3 Reactions of Hydrosilanes with Carbonyl Compounds and Imines

2.4 Reactions of Hydrosilanes with α-Diazo Carbonyl Compounds

2.5 Miscellaneous Transformations from the Nano Au-Catalyzed Activation­ of Hydrosilanes

3 Activation of Disilanes

3.1 Disilylation of Alkynes

3.2 Reactions of 1,1,2,2-Tetramethyldisilane with Alkynes

4 Activation of Diboranes

4.1 Diborylation of Alkenes

4.2 Diborylation of Alkynes

4.3 Diborylation of Allenes

4.4 Diborylation of Methylenecyclopropanes

5 Activation of Silylboranes

5.1 Silaboration of Alkynes

5.2 Silaboration of Allenes

5.3 Silaboration of Unactivated Epoxides and Oxetanes

5.4 Reactions of Silylboranes with Aromatic Carbonyl Compounds

6 Conclusions and Future Perspectives

Key words

Au nanoparticles - nanoporous Au - heterogeneous catalysis - hydrosilylation - disilylation - diborylation - silaboration

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