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Rh-catalyzed oxidative coupling between primary and secondary benzamides and alkynes: synthesis of polycyclic amides.
J Org Chem. 2010 Nov 05; 75(21):7487-90.JO

Abstract

A methodology for the high yield and facile synthesis of isoquinolones from benzamides and alkynes via the oxidative ortho C-H activation of benzamides has been developed. Ag(2)CO(3) proved to be an optimal oxidant when MeCN was used as a solvent, and [RhCp*Cl(2)](2) was utilized as an efficient catalyst. Both N-alkyl and N-aryl secondary benzamides can be applied as effective substrates. Furthermore, primary benzamides react with two alkyne units, leading to tricyclic products via double C-H activation and oxidative coupling. The reactivity of the structurally related 1-hydroxyisoquinoline was also demonstrated, where both N- and O-containing rhodacyclic intermediates can be generated, leading to the construction of different O- or N-containing heterocycles.

Authors+Show Affiliations

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China 116023.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

20923219

Citation

Song, Guoyong, et al. "Rh-catalyzed Oxidative Coupling Between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides." The Journal of Organic Chemistry, vol. 75, no. 21, 2010, pp. 7487-90.
Song G, Chen D, Pan CL, et al. Rh-catalyzed oxidative coupling between primary and secondary benzamides and alkynes: synthesis of polycyclic amides. J Org Chem. 2010;75(21):7487-90.
Song, G., Chen, D., Pan, C. L., Crabtree, R. H., & Li, X. (2010). Rh-catalyzed oxidative coupling between primary and secondary benzamides and alkynes: synthesis of polycyclic amides. The Journal of Organic Chemistry, 75(21), 7487-90. https://doi.org/10.1021/jo101596d
Song G, et al. Rh-catalyzed Oxidative Coupling Between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides. J Org Chem. 2010 Nov 5;75(21):7487-90. PubMed PMID: 20923219.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rh-catalyzed oxidative coupling between primary and secondary benzamides and alkynes: synthesis of polycyclic amides. AU - Song,Guoyong, AU - Chen,Dan, AU - Pan,Cheng-Ling, AU - Crabtree,Robert H, AU - Li,Xingwei, PY - 2010/10/7/entrez PY - 2010/10/7/pubmed PY - 2011/2/16/medline SP - 7487 EP - 90 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 21 N2 - A methodology for the high yield and facile synthesis of isoquinolones from benzamides and alkynes via the oxidative ortho C-H activation of benzamides has been developed. Ag(2)CO(3) proved to be an optimal oxidant when MeCN was used as a solvent, and [RhCp*Cl(2)](2) was utilized as an efficient catalyst. Both N-alkyl and N-aryl secondary benzamides can be applied as effective substrates. Furthermore, primary benzamides react with two alkyne units, leading to tricyclic products via double C-H activation and oxidative coupling. The reactivity of the structurally related 1-hydroxyisoquinoline was also demonstrated, where both N- and O-containing rhodacyclic intermediates can be generated, leading to the construction of different O- or N-containing heterocycles. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20923219/Rh_catalyzed_oxidative_coupling_between_primary_and_secondary_benzamides_and_alkynes:_synthesis_of_polycyclic_amides_ L2 - https://doi.org/10.1021/jo101596d DB - PRIME DP - Unbound Medicine ER -