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Rapid and efficient Pd-catalyzed Sonogashira coupling of aryl chlorides.
J Org Chem. 2008 Aug 01; 73(15):6037-40.JO

Abstract

An efficient and effective microwave-assisted cross-coupling of terminal alkynes with various aryl chlorides including sterically hindered, electron-rich, electron-neutral, and electron-deficient aryl chloride is developed. It proceeds faster and generally gives good to excellent yields and also can be extended successfully to the Suzuki coupling and Buchwald-Hartwig amination, as well as the Heck coupling with inert aryl chlorides. The short reaction times and simple reaction conditions coupling with a broad substrate scope render this method particularly attractive for the efficient preparation of biologically and medicinally interesting molecules.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Huang H
Drug Discovery and Design Centre, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, and Graduate School, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
Liu H
No affiliation info available
Jiang H
No affiliation info available
Chen K
No affiliation info available

MeSH

AcetyleneAlkynesCatalysisChloridesMethylationMicrowavesMolecular StructurePalladiumStereoisomerismTime Factors

Pub Type(s)

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

Language

eng

PubMed ID

18598086

Citation

Huang, He, et al. "Rapid and Efficient Pd-catalyzed Sonogashira Coupling of Aryl Chlorides." The Journal of Organic Chemistry, vol. 73, no. 15, 2008, pp. 6037-40.
Huang H, Liu H, Jiang H, et al. Rapid and efficient Pd-catalyzed Sonogashira coupling of aryl chlorides. J Org Chem. 2008;73(15):6037-40.
Huang, H., Liu, H., Jiang, H., & Chen, K. (2008). Rapid and efficient Pd-catalyzed Sonogashira coupling of aryl chlorides. The Journal of Organic Chemistry, 73(15), 6037-40. https://doi.org/10.1021/jo800994f
Huang H, et al. Rapid and Efficient Pd-catalyzed Sonogashira Coupling of Aryl Chlorides. J Org Chem. 2008 Aug 1;73(15):6037-40. PubMed PMID: 18598086.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rapid and efficient Pd-catalyzed Sonogashira coupling of aryl chlorides. AU - Huang,He, AU - Liu,Hong, AU - Jiang,Hualiang, AU - Chen,Kaixian, Y1 - 2008/07/04/ PY - 2008/7/5/pubmed PY - 2008/9/27/medline PY - 2008/7/5/entrez SP - 6037 EP - 40 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 15 N2 - An efficient and effective microwave-assisted cross-coupling of terminal alkynes with various aryl chlorides including sterically hindered, electron-rich, electron-neutral, and electron-deficient aryl chloride is developed. It proceeds faster and generally gives good to excellent yields and also can be extended successfully to the Suzuki coupling and Buchwald-Hartwig amination, as well as the Heck coupling with inert aryl chlorides. The short reaction times and simple reaction conditions coupling with a broad substrate scope render this method particularly attractive for the efficient preparation of biologically and medicinally interesting molecules. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/18598086/Rapid_and_efficient_Pd_catalyzed_Sonogashira_coupling_of_aryl_chlorides_ L2 - https://doi.org/10.1021/jo800994f DB - PRIME DP - Unbound Medicine ER -