Highly Selective Cross-Coupling Reactions of Organosilicon Compounds Mediated by Fluoride Ion and a Palladium Catalyst

Abstract

Organosilicon compounds couple with organic halides or triflates in the presence of a fluoride ion promoter and a palladium catalyst. This reaction is in general highly chemoselective and stereospecific. In addition to carbon-carbon bond formation, carbon-silicon bond formation is realized. Synthetic examples mainly from our Laboratories are reviewed with the emphasis on the mechanism and stereochemistry of transmetalation from silicon to palladium. 1. Introduction 2. Cross-Coupling Reactions of Alkenylsilanes with Organic Halides 3. Dienyne Synthesis with Stannyl(silyl)ethyne 4. Cross-Coupling Reactions of Arylsilanes 5. Diaryl Ketone Synthesis Using Arylsilanes and Carbon Monoxide 6. Allylation of Organic Halides 7. Silylation and Methylation of Organic Halides 8. Cross-Coupling Reactions of Organic Triflates with Organosilicon Compounds 9. Stereochemistry of Cross-Coupling Reaction 10. Mechanism of Transmetalation of Alkenylsilanes 11. Conclusion