Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes
Publication type: Journal Article
Publication date: 2003-08-23
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
12968885
Organic Chemistry
Abstract
An efficient synthesis of highly substituted naphthalenes has been developed by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon-carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation of the alkyne, followed by intramolecular Heck olefination and double-bond isomerization. This method accommodates a variety of functional groups and affords the anticipated highly substituted naphthalenes and carbazoles in good to excellent yields.
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Total citations:
69
Citations from 2024:
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GOST
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Huang Q., Larock R. C. Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes // Journal of Organic Chemistry. 2003. Vol. 68. No. 19. pp. 7342-7349.
GOST all authors (up to 50)
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Huang Q., Larock R. C. Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes // Journal of Organic Chemistry. 2003. Vol. 68. No. 19. pp. 7342-7349.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo034449x
UR - https://doi.org/10.1021/jo034449x
TI - Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes
T2 - Journal of Organic Chemistry
AU - Huang, Qinhua
AU - Larock, Richard C.
PY - 2003
DA - 2003/08/23
PB - American Chemical Society (ACS)
SP - 7342-7349
IS - 19
VL - 68
PMID - 12968885
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2003_Huang,
author = {Qinhua Huang and Richard C. Larock},
title = {Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes},
journal = {Journal of Organic Chemistry},
year = {2003},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/jo034449x},
number = {19},
pages = {7342--7349},
doi = {10.1021/jo034449x}
}
Cite this
MLA
Copy
Huang, Qinhua, and Richard C. Larock. “Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes.” Journal of Organic Chemistry, vol. 68, no. 19, Aug. 2003, pp. 7342-7349. https://doi.org/10.1021/jo034449x.