Palladium-Catalysed Reactions of Organotin Compounds

Abstract

Palladium-catalysed reactions involving organotin compounds are of rapidly increasing importance in organic synthesis. Carbon-carbon bond formation via cross-coupling reactions is of primary interest in view of the variety of functionalities which can be used. A variety of applications in natural product synthesis have been described, and intramolecular reactions can be used for the formation of small, medium and large rings. Reactions involving additions of tin-element bonds to multiply bonded systems are also of increasing significance. Although "general-purpose" catalysts are available, specific catalysts are often required for certain applications. 1. Introduction 2. Palladium-Catalysed Substitution Reactions Involving Residues R′ 2.1. R′ = Various 2.2. R′ = Vinyl 2.3. R′ = Aryl 2.4. R′ = Heteroaryl 2..5. R′ = Allyl 2.6. R′ = Alkynyl 2.7. R′= Other Organic Residues 2.8. R′ = Residue Containing Elements other than Carbon 2.8.1. Group 13 Elements 2.8.2. Other Group 14 Elements 2.8.3. Group 15 Elements 2.8.4. Group 16 Elements 2.8.5. R′ = Cl 3. Palladium-Catalysed Addition Reactions Involving Sn-E Bonds 3.1. E=H 3.2. E = SnR′3 3.3. E = SiR′3, GeR′3 3.4. E = Other Elements 4. The Choice of Tin Reagent and Catalyst 5. Conclusion