A novel Zinc-catalyzed Cadiot-Chodkiewicz cross-coupling reaction of terminal alkynes with 1-bromoalkynes in ethanol solvent

[Display omitted] •The methodology makes use of the first non-toxic and ecofriendly Zn catalyst with an inexpensive amino acid ligand L-proline.•The important aspect is the use of ecofriendly ethanol as the solvent for the reaction.•Moderate to good yields for some aryl as well as heteroaryl substra...

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Bibliographic Details
Published in:Molecular catalysis 2017-10, Vol.440, p.140-147
Main Authors: Krishnan, K. Keerthi, Ujwaldev, S.M., Thankachan, Amrutha P., Harry, Nissy Ann, Gopinathan, Anilkumar
Format: Article
Language:English
Subjects:
1,3-diynes
C[sbnd]C coupling
Cadiot-Chodkiewicz reaction
Cross-coupling
Zinc catalysis
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Summary:[Display omitted] •The methodology makes use of the first non-toxic and ecofriendly Zn catalyst with an inexpensive amino acid ligand L-proline.•The important aspect is the use of ecofriendly ethanol as the solvent for the reaction.•Moderate to good yields for some aryl as well as heteroaryl substrates. A novel Et2Zn/L-proline catalyzed synthesis of symmetrical as well as unsymmetrical buta-1,3-diynes by the cross-coupling of terminal alkynes with 1-bromo alkynes in ethanol solvent was developed in good yields under simple and mild reaction conditions. The use of relatively non toxic and ecofriendly nature of Zn, inexpensive amino acid ligand L-proline and environmentally benign solvent EtOH make this protocol a better alternative for the synthesis of 1,3-diynes. The scope and limitations of this protocol were investigated.
ISSN:2468-8231
2468-8231
DOI:10.1016/j.mcat.2017.07.021