Course Guarantor
Miroslav Soural
Form of course completion:
Exam
Annotation:
Carbon-carbon bond forming reactions are arguably the most important processes in chemistry, as they represent key steps in the building of complex molecules from simple precursors. Among these reactions, metal-catalyzed cross-coupling reactions are extensively employed in a wide range of areas of preparative organic chemistry, ranging from the synthesis of complex natural products, to supramolecular chemistry, and materials science. This course is dedicated to overview of all the most frequent types of metall-catalyzed cross-coupling reactions.
Content:
- Introduction to cross-coupling reactions: historical perspective, catalytic cycle
- Palladium- or nickel-catalyzed cross-coupling with organometals containing Zn, Mg, Al, and Zi: Systematic survey of palladium- or nickel-catalyzed cross-coupling, assymetric cross-coupling, palladium-catalyzed tandem processes involving cross-coupling reactions, mechanism of cross-coupling
- Cross-coupling reactions of organoboron compounds with organic halides: Preparation of organoboron compounds, palladium-catalyzed reactions of organoboron compounds and their mechanism, cross-coupling reactions of organoboron compounds
- Palladium-catalyzed coupling of organyl halides to alkenes – the Heck reaction: Principles, cascade reactions and multiple couplings, related palladium-catalyzed reactions, enantioselective Heck-type reactions
- Organotin reagents in cross-coupling: Stille coupling of alkenyltins, reactions of substrates where tin is attached to a heterocyclic ring, reactions of aryl- and alkyltins, Reactions involving various types of tetraorganotin, reactions of allyl- allenyl- and propargyltins, related palladium-catalyzed reactions, reactions induced by copper, nickel-catalyzed reactions
- Cross-coupling reactions to sp carbon atoms: Cross-coupling reactions of alkynylmetal reagents with sp2 carbon atoms, transition-metal-catalyzed cross-coupling
- Carbometallation reaction: Carbometallation of alkynes, allenes, enynes, alkenes, enantioselective carbometallation of alkenes
- Palladium-catalyzed 1,4-additions to conjugated dienes: Palladium(O)-catalyzed reactions, palladium(II)-catalyzed reactions
- Carbon-carbon bond formation reactions mediated by organozinc reagents: Uncatalyzed cross-coupling reactions, copper-catalyzed cross-coupling reactions, Transition-metal-catalyzed cross-coupling reactions
- Organosilicon compounds in cross-coupling reactions: Coupling reactions of alkenylsilanes, arylsilanes, alkynylsilanes, disilanes, alkylsilanes, allylsilanes, coupling reactions without fluoride ion
- Palladium-catalyzed coupling reactions of propargylic compounds
Literature:
- A. de Meijere, François Diederich. Metal-Catalyzed Cross-Coupling Reactions. Wiley-VCH, 2004
- Norio Myiaura. Cross-Coupling Reactions A Practical Guide. Springer, 2002.
- François Diederich, Peter J. Stang. Metal-Catalyzed Cross-Coupling Reactions. John Wiley and Sons, 1998.
