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Palladacycle-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl chlorides under air.
J Org Chem. 2013 May 03; 78(9):4543-50.JO

Abstract

A highly efficient and practical protocol for palladacycle-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl chlorides was developed. The reaction could proceed smoothly in air within 3 h under optimized reaction conditions (1 mol % of palladacycle, 4 mol % of Xphos, 2.0 equiv of K2CO3 in xylene/H2O), affording the corresponding internal alkynes in mostly good to excellent yields. Remarkably, this result represents the first successful examples of this type of decarboxylative cross-coupling using electron-poor, electron-neutral and even inactive sterically hindered electron-rich aryl chlorides as the starting materials.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li X
The College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China.
Yang F
No affiliation info available
Wu Y
No affiliation info available

MeSH

AirAlkynesCarboxylic AcidsChemistry Techniques, SyntheticDecarboxylationFerrous CompoundsHydrocarbons, AromaticHydrocarbons, ChlorinatedMolecular StructureOrganometallic CompoundsPalladium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23573947

Citation

Li, Xiang, et al. "Palladacycle-catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids With Aryl Chlorides Under Air." The Journal of Organic Chemistry, vol. 78, no. 9, 2013, pp. 4543-50.
Li X, Yang F, Wu Y. Palladacycle-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl chlorides under air. J Org Chem. 2013;78(9):4543-50.
Li, X., Yang, F., & Wu, Y. (2013). Palladacycle-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl chlorides under air. The Journal of Organic Chemistry, 78(9), 4543-50. https://doi.org/10.1021/jo400574d
Li X, Yang F, Wu Y. Palladacycle-catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids With Aryl Chlorides Under Air. J Org Chem. 2013 May 3;78(9):4543-50. PubMed PMID: 23573947.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladacycle-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl chlorides under air. AU - Li,Xiang, AU - Yang,Fan, AU - Wu,Yangjie, Y1 - 2013/04/22/ PY - 2013/4/12/entrez PY - 2013/4/12/pubmed PY - 2013/12/18/medline SP - 4543 EP - 50 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 9 N2 - A highly efficient and practical protocol for palladacycle-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl chlorides was developed. The reaction could proceed smoothly in air within 3 h under optimized reaction conditions (1 mol % of palladacycle, 4 mol % of Xphos, 2.0 equiv of K2CO3 in xylene/H2O), affording the corresponding internal alkynes in mostly good to excellent yields. Remarkably, this result represents the first successful examples of this type of decarboxylative cross-coupling using electron-poor, electron-neutral and even inactive sterically hindered electron-rich aryl chlorides as the starting materials. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23573947/Palladacycle_catalyzed_decarboxylative_coupling_of_alkynyl_carboxylic_acids_with_aryl_chlorides_under_air_ L2 - https://doi.org/10.1021/jo400574d DB - PRIME DP - Unbound Medicine ER -