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. 2009 Oct 1;2009(16):2565-2582.
doi: 10.1055/s-0029-1217747.

Catalytic Addition of Simple Alkenes to Carbonyl Compounds Using Group 10 Metals

Chun-Yu Ho  1 , Kristin D Schleicher, Timothy F Jamison
Affiliations

Catalytic Addition of Simple Alkenes to Carbonyl Compounds Using Group 10 Metals

Chun-Yu Ho et al. Synlett. .

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.

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Figures

Scheme 1
Scheme 1
Traditional Methods of Synthesis of Homoallylic and Allylic Alcohols from Simple Alkenes and Aldehydes: Carbonyl-Ene and Prins Reactions
Scheme 2
Scheme 2
Complementarity of Catalytic Alkene Addition to Aldehyde
Scheme 3
Scheme 3
Intra- and Intermolecular Competition Experiments Using α–Olefins Versus 1,1-Disubstituted Alkenes Under Ni(0) Catalysis.
Scheme 4
Scheme 4
Proposed Mechanism for the Ni(0)-Catalyzed Synthesis of Homoallylic and Allylic Alcohol Products
Scheme 5
Scheme 5
Ligand Effect on Coupling Product Selectivity
Scheme 6
Scheme 6
Proposed Mechanism for Highly Selective Coupling of Alkenes and Aldehydes Catalyzed by Ni(NHC)P(OPh)3: Synergy between a Strong σ-Donor and a Strong π-Aceeptor
Scheme 7
Scheme 7
Highly Selective Synthesis of Homoallylic or Allylic Alcohols: Ligand-Controlled Ni(0)-Catalyzed Coupling of α-Olefins, Aldehydes and Silyl Triflates
Scheme 8
Scheme 8
Proposal for IPr-Controlled Azanickellacycle Formation
Scheme 9
Scheme 9
Traditional Approaches for Synthesis of δ,ω- or γ,δ-Unsaturated Carbonyl Compounds Using Lewis Acid-Catalyzed Conditions and Organometallic Reagents
Scheme 10
Scheme 10
Proposed Mechanism for the Ni(0)-Catalyzed, Highly Selective Alkene Addition to Conjugate Systems
Scheme 11
Scheme 11
Proposed Mechanism for the Ni(0)-Catalyzed Intramolecular Coupling of 3-Styrylcyclobutanones
See this image and copyright information in PMC

References

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