Waste-free synthesis of condensed heterocyclic compounds by rhodium-catalyzed oxidative coupling of substituted arene or heteroarene carboxylic acids with alkynes.
Publication type: Journal Article
Publication date: 2009-04-03
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
19388716
Organic Chemistry
Abstract
The direct oxidative coupling of 2-amino- and 2-hydroxybenzoic acids with internal alkynes proceeds efficiently in the presence of a rhodium/copper catalyst system under air to afford the corresponding 8-substituted isocoumarin derivatives, some of which exhibit solid-state fluorescence. Depending on conditions, 4-ethenylcarbazoles can be synthesized selectively from 2-(arylamino)benzoic acids. The oxidative coupling reactions of heteroarene carboxylic acids as well as aromatic diacids with an alkyne are also described.
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Metrics
182
Total citations:
182
Citations from 2024:
7
(3.85%)
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MLA
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GOST
Copy
Shimizu M. et al. Waste-free synthesis of condensed heterocyclic compounds by rhodium-catalyzed oxidative coupling of substituted arene or heteroarene carboxylic acids with alkynes. // Journal of Organic Chemistry. 2009. Vol. 74. No. 9. pp. 3478-3483.
GOST all authors (up to 50)
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Shimizu M., Hirano K., Satoh T., Miura M. Waste-free synthesis of condensed heterocyclic compounds by rhodium-catalyzed oxidative coupling of substituted arene or heteroarene carboxylic acids with alkynes. // Journal of Organic Chemistry. 2009. Vol. 74. No. 9. pp. 3478-3483.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo900396z
UR - https://doi.org/10.1021/jo900396z
TI - Waste-free synthesis of condensed heterocyclic compounds by rhodium-catalyzed oxidative coupling of substituted arene or heteroarene carboxylic acids with alkynes.
T2 - Journal of Organic Chemistry
AU - Shimizu, M.
AU - Hirano, Koji
AU - Satoh, Tetsuya
AU - Miura, Masahiro
PY - 2009
DA - 2009/04/03
PB - American Chemical Society (ACS)
SP - 3478-3483
IS - 9
VL - 74
PMID - 19388716
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2009_Shimizu,
author = {M. Shimizu and Koji Hirano and Tetsuya Satoh and Masahiro Miura},
title = {Waste-free synthesis of condensed heterocyclic compounds by rhodium-catalyzed oxidative coupling of substituted arene or heteroarene carboxylic acids with alkynes.},
journal = {Journal of Organic Chemistry},
year = {2009},
volume = {74},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/jo900396z},
number = {9},
pages = {3478--3483},
doi = {10.1021/jo900396z}
}
Cite this
MLA
Copy
Shimizu, M., et al. “Waste-free synthesis of condensed heterocyclic compounds by rhodium-catalyzed oxidative coupling of substituted arene or heteroarene carboxylic acids with alkynes..” Journal of Organic Chemistry, vol. 74, no. 9, Apr. 2009, pp. 3478-3483. https://doi.org/10.1021/jo900396z.