Abstract
Recent advances using nickel complexes in the activation of unactivated
monosubstituted olefins for catalytic intermolecular carbon-carbon
bond-forming reactions with carbonyl compounds, such as simple aldehydes,
isocyanates, and conjugated aldehydes and ketones, are discussed.
In these reactions, the olefins function as vinyl- and allylmetal
equivalents, providing a new strategy for organic synthesis. Current
limitations and the outlook for this new strategy are also discussed.
1 Introduction
2 Carbonyl-Ene-Type Reactions
2.1 Reactions Catalyzed by Group 10 Cationic Complexes as Lewis
Acids
2.2 Reactions Catalyzed by Low-Valent Nickel(0) Complexes
3 Unactivated Monosubstituted Alkenes as Vinylmetal Equivalents
3.1 Intramolecular Reactions with Aldehydes and Ketones
3.2 Intermolecular Reactions with Aldehydes
3.3 Synthesis of Acrylamides with Isocyanates
3.4 Conjugate Addition to α,β-Unsaturated
Aldehydes and Ketones
4 Intramolecular Insertion of Alkenes into Cyclobutanones
5 Limitations and Outlook
Key words
alkenes - transition-metal catalysis - carbon-carbon bond
formation - carbonyl-ene reactions - addition
reactions
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