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Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: regioselective oxidative cycloaddition of aromatic amides to alkynes.
J Am Chem Soc. 2011 Sep 28; 133(38):14952-5.JA

Abstract

Although the pioneering example of ortho metalation involving cleavage of C-H bonds was achieved using a nickel complex (Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544), no examples of catalysis using nickel complexes have been reported. In this work, the Ni-catalyzed transformation of ortho C-H bonds utilizing chelation assistance, such as oxidative cycloaddition of aromatic amides with alkynes, has been achieved.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Shiota H
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, Japan.
Ano Y
No affiliation info available
Aihara Y
No affiliation info available
Fukumoto Y
No affiliation info available
Chatani N
No affiliation info available

MeSH

AlkynesAmidesCatalysisChelating AgentsCyclizationIsoquinolinesMolecular StructureNickelOrganometallic CompoundsOxidation-ReductionStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21875095

Citation

Shiota, Hirotaka, et al. "Nickel-catalyzed Chelation-assisted Transformations Involving Ortho C-H Bond Activation: Regioselective Oxidative Cycloaddition of Aromatic Amides to Alkynes." Journal of the American Chemical Society, vol. 133, no. 38, 2011, pp. 14952-5.
Shiota H, Ano Y, Aihara Y, et al. Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: regioselective oxidative cycloaddition of aromatic amides to alkynes. J Am Chem Soc. 2011;133(38):14952-5.
Shiota, H., Ano, Y., Aihara, Y., Fukumoto, Y., & Chatani, N. (2011). Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: regioselective oxidative cycloaddition of aromatic amides to alkynes. Journal of the American Chemical Society, 133(38), 14952-5. https://doi.org/10.1021/ja206850s
Shiota H, et al. Nickel-catalyzed Chelation-assisted Transformations Involving Ortho C-H Bond Activation: Regioselective Oxidative Cycloaddition of Aromatic Amides to Alkynes. J Am Chem Soc. 2011 Sep 28;133(38):14952-5. PubMed PMID: 21875095.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: regioselective oxidative cycloaddition of aromatic amides to alkynes. AU - Shiota,Hirotaka, AU - Ano,Yusuke, AU - Aihara,Yoshinori, AU - Fukumoto,Yoshiya, AU - Chatani,Naoto, Y1 - 2011/09/07/ PY - 2011/8/31/entrez PY - 2011/8/31/pubmed PY - 2012/1/6/medline SP - 14952 EP - 5 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 133 IS - 38 N2 - Although the pioneering example of ortho metalation involving cleavage of C-H bonds was achieved using a nickel complex (Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544), no examples of catalysis using nickel complexes have been reported. In this work, the Ni-catalyzed transformation of ortho C-H bonds utilizing chelation assistance, such as oxidative cycloaddition of aromatic amides with alkynes, has been achieved. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/21875095/Nickel_catalyzed_chelation_assisted_transformations_involving_ortho_C_H_bond_activation:_regioselective_oxidative_cycloaddition_of_aromatic_amides_to_alkynes_ L2 - https://doi.org/10.1021/ja206850s DB - PRIME DP - Unbound Medicine ER -