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Palladium-catalyzed cross-coupling of electron-poor terminal alkynes with arylboronic acids under ligand-free and aerobic conditions.
J Org Chem. 2010 Aug 20; 75(16):5635-42.JO

Abstract

Palladium-catalyzed cross-coupling reaction of terminal alkynes with arylboronic acids has been described. In the presence of Pd(OAc)(2) and Ag(2)O, a variety of terminal alkynes, including electron-poor terminal alkynes, smoothly underwent the reaction with numerous boronic acids to afford the corresponding internal alkynes in moderate to good yields. Moreover, this methodology was applied to the synthesis of 1H-isochromenes and diynes. It is noteworthy that the reaction proceeds under ligand-free and relative lower loading Pd conditions, and the maximal TONs (turnover numbers) of the reaction are up to 720,000.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhou MB
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, China.
Wei WT
No affiliation info available
Xie YX
No affiliation info available
Lei Y
No affiliation info available
Li JH
No affiliation info available

MeSH

AlkynesBoronic AcidsCatalysisElectronsMolecular StructureOrganometallic CompoundsPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20704435

Citation

Zhou, Ming-Bo, et al. "Palladium-catalyzed Cross-coupling of Electron-poor Terminal Alkynes With Arylboronic Acids Under Ligand-free and Aerobic Conditions." The Journal of Organic Chemistry, vol. 75, no. 16, 2010, pp. 5635-42.
Zhou MB, Wei WT, Xie YX, et al. Palladium-catalyzed cross-coupling of electron-poor terminal alkynes with arylboronic acids under ligand-free and aerobic conditions. J Org Chem. 2010;75(16):5635-42.
Zhou, M. B., Wei, W. T., Xie, Y. X., Lei, Y., & Li, J. H. (2010). Palladium-catalyzed cross-coupling of electron-poor terminal alkynes with arylboronic acids under ligand-free and aerobic conditions. The Journal of Organic Chemistry, 75(16), 5635-42. https://doi.org/10.1021/jo101063p
Zhou MB, et al. Palladium-catalyzed Cross-coupling of Electron-poor Terminal Alkynes With Arylboronic Acids Under Ligand-free and Aerobic Conditions. J Org Chem. 2010 Aug 20;75(16):5635-42. PubMed PMID: 20704435.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed cross-coupling of electron-poor terminal alkynes with arylboronic acids under ligand-free and aerobic conditions. AU - Zhou,Ming-Bo, AU - Wei,Wen-Ting, AU - Xie,Ye-Xiang, AU - Lei,Yong, AU - Li,Jin-Heng, PY - 2010/8/14/entrez PY - 2010/8/14/pubmed PY - 2010/12/14/medline SP - 5635 EP - 42 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 16 N2 - Palladium-catalyzed cross-coupling reaction of terminal alkynes with arylboronic acids has been described. In the presence of Pd(OAc)(2) and Ag(2)O, a variety of terminal alkynes, including electron-poor terminal alkynes, smoothly underwent the reaction with numerous boronic acids to afford the corresponding internal alkynes in moderate to good yields. Moreover, this methodology was applied to the synthesis of 1H-isochromenes and diynes. It is noteworthy that the reaction proceeds under ligand-free and relative lower loading Pd conditions, and the maximal TONs (turnover numbers) of the reaction are up to 720,000. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20704435/Palladium_catalyzed_cross_coupling_of_electron_poor_terminal_alkynes_with_arylboronic_acids_under_ligand_free_and_aerobic_conditions_ L2 - https://doi.org/10.1021/jo101063p DB - PRIME DP - Unbound Medicine ER -