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DOI: 10.1055/s-0032-1316913
From the Development of Catalysts for Alkyne and Alkyne–Nitrile [2+2+2] Cycloaddition Reactions to Their Use in Polymerization Reactions
Publikationsverlauf
Received: 07. Februar 2013
Accepted after revision: 18. März 2013
Publikationsdatum:
12. April 2013 (online)
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Abstract
Several systems consisting of a ligand, a metal compound, and zinc have been developed as catalysts for alkyne cycloaddition reactions and alkyne–nitrile co-cycloaddition reactions. N-Heterocyclic carbene (NHC)–iron(III) chloride–zinc, NHC–cobalt(II) chloride-zinc, and 2-{[(2,6-diisopropylphenyl)imino]methyl}pyridine (dipimp)–iron(III) chloride hexahydrate–zinc systems catalyzed intramolecular cyclotrimerization reactions of alkynes. The dipimp–cobalt(II) chloride hexahydrate–zinc system catalyzed cycloaddition reactions of a variety of alkynes in intramolecular, partially intramolecular, and fully intermolecular fashions. The ethane-1,2-diylbis(diphenylphosphine)–cobalt(II) chloride hexahydrate–zinc system was effective in catalyzing the [2 + 2 + 2] co-cycloaddition of diynes with nitriles. Nickel complexes with an ionic liquid-tagged ligand converted 1,6-diynes into the corresponding cyclooctatetraenes in a toluene–ionic liquid biphasic system in the presence of zinc. The dipimp–nickel(II) chloride hexahydrate–zinc catalyst polymerized 1,6-diynes to form conjugated polyene cyclic polymers. These results and their applications in synthesis, including controlled polymerization reactions, are described.
1 Introduction
2 Alkyne [2+2+2] Cycloaddition
2.1 Development of N-Heterocyclic Carbene–Cobalt or Iron Compound–Zinc Catalyst Systems
2.2 Development of 2-{[(2,6-Diisopropylphenyl)imino]methyl}pyridine–Cobalt or Iron Salt–Zinc Catalyst Systems
2.2.1 Development of 2-{[(2,6-Diisopropylphenyl)imino]methyl}pyridine–Iron Chloride–Zinc Catalyst Systems
2.2.2 Development of the 2-{[(2,6-Diisopropylphenyl)imino]methyl}pyridine–Iron Chloride Hexahydrate–Zinc Catalyst System
2.3 The 2-{[(2,6-Diisopropylphenyl)imino]methyl}pyridine–Cobalt(II) Chloride Hexahydrate–Zinc Catalyst System
2.3.1 Reactivity and Functional Group Compatibility
2.3.2 Catalyst Activation
3 Alkyne–Nitrile [2+2+2] Co-cycloaddition
4 Applications
4.1 Uses in Organic Synthesis
4.2 Use as a Method for Polymer Synthesis
4.2.1 Preparation of Diverse Polymerizable Molecules (a Monomer Library)
4.2.2 Use in Polymer Functionalization
4.2.3 Use as a Polymerization Reaction
5 Other Reactions
5.1 Nickel-Catalyzed [2+2+2+2] Cycloaddition and Cycloaddition Polymerization of 1,6-Diynes
5.2 Hydroalkynylation of Internal Alkynes
6 Conclusion
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Recent examples of cobalt salt/Zn-catalyzed reactions other than cyclotrimerizations; for Alder–ene reactions of alkynes, see:
For hydroalkynylation reactions, see:
For addition of silylacetylenes to enones and dienones, see:
For Diels–Alder reactions, see:
For 1,4-hydrovinylation reactions, see:
For reductive coupling reactions, see:
For titanium, see:
For other metals, see:
For catalysis using dipimp, see:
For polymerizations, see:
For cycloadditions catalyzed by CoI2(PPh)2–Zn or CoI2(dppe)–Zn, see:
For related intramolecular reactions catalyzed by CoI2(dppe)–Zn, see:
For recent reports on iron-based instant catalysts, see:
For reviews, see :
For recent examples, see:
For the divalent titanium-mediated synthesis, see: