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Rhodium(III)-catalyzed isoquinolone synthesis: the N-O bond as a handle for C-N bond formation and catalyst turnover.
J Am Chem Soc. 2010 May 26; 132(20):6908-9.JA

Abstract

An external-oxidant-free process to access the isoquinolone motif via cross-coupling/cyclization of benzhydroxamic acid with alkynes is described. The reaction features a regioselective cleavage of a C-H bond on the benzhydroxamic acid coupling partner as well as a regioselective alkyne insertion. Mechanistic studies point out the important involvement of a N-O bond as a tool for C-N bond formation and catalyst turnover.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Guimond N
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada. nguim025@uottawa.ca
Gouliaras C
No affiliation info available
Fagnou K
No affiliation info available

MeSH

AlkynesCarbonCatalysisHydroxamic AcidsNitrogenOxygenQuinolonesRhodium

Pub Type(s)

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

Language

eng

PubMed ID

20433170

Citation

Guimond, Nicolas, et al. "Rhodium(III)-catalyzed Isoquinolone Synthesis: the N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover." Journal of the American Chemical Society, vol. 132, no. 20, 2010, pp. 6908-9.
Guimond N, Gouliaras C, Fagnou K. Rhodium(III)-catalyzed isoquinolone synthesis: the N-O bond as a handle for C-N bond formation and catalyst turnover. J Am Chem Soc. 2010;132(20):6908-9.
Guimond, N., Gouliaras, C., & Fagnou, K. (2010). Rhodium(III)-catalyzed isoquinolone synthesis: the N-O bond as a handle for C-N bond formation and catalyst turnover. Journal of the American Chemical Society, 132(20), 6908-9. https://doi.org/10.1021/ja102571b
Guimond N, Gouliaras C, Fagnou K. Rhodium(III)-catalyzed Isoquinolone Synthesis: the N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover. J Am Chem Soc. 2010 May 26;132(20):6908-9. PubMed PMID: 20433170.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium(III)-catalyzed isoquinolone synthesis: the N-O bond as a handle for C-N bond formation and catalyst turnover. AU - Guimond,Nicolas, AU - Gouliaras,Christina, AU - Fagnou,Keith, PY - 2010/5/4/entrez PY - 2010/5/4/pubmed PY - 2010/8/12/medline SP - 6908 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 20 N2 - An external-oxidant-free process to access the isoquinolone motif via cross-coupling/cyclization of benzhydroxamic acid with alkynes is described. The reaction features a regioselective cleavage of a C-H bond on the benzhydroxamic acid coupling partner as well as a regioselective alkyne insertion. Mechanistic studies point out the important involvement of a N-O bond as a tool for C-N bond formation and catalyst turnover. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20433170/Rhodium_III__catalyzed_isoquinolone_synthesis:_the_N_O_bond_as_a_handle_for_C_N_bond_formation_and_catalyst_turnover_ L2 - https://doi.org/10.1021/ja102571b DB - PRIME DP - Unbound Medicine ER -