Palladium‐Catalyzed Formation of Highly Substituted Naphthalenes from Arene and Alkyne Hydrocarbons
Publication type: Journal Article
Publication date: 2008-07-21
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
18551492
General Chemistry
Catalysis
Organic Chemistry
Abstract
Several highly substituted naphthalenes 3 have been synthesized in a one‐pot reaction by treatment of arenes 1 with alkynes 2 in the presence of palladium acetate and silver acetate. In this Pd‐catalyzed protocol, an arene provides a benzo source for the construction of a naphthalene core through twofold aryl CH bond activation. Reaction of triphenylphosphine with diphenylethyne (2 a) under the catalysis of PdIV complexes produced 1,2,3,4‐tetraphenylnaphthalene (3 ba) in 62 % yield. Here, triphenylphosphine undergoes one aryl CP bond cleavage and one aryl CH bond activation to serve as a benzo moiety. Crystal structures of cycloadducts 3 ea, 3 ga, and 3 ac have been analyzed. The twisted naphthalenes arise not only from the overcrowded substituents but also from the contribution of the CH3–π interaction.
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117
Total citations:
117
Citations from 2025:
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GOST
Copy
Wu Y. et al. Palladium‐Catalyzed Formation of Highly Substituted Naphthalenes from Arene and Alkyne Hydrocarbons // Chemistry - A European Journal. 2008. Vol. 14. No. 22. pp. 6697-6703.
GOST all authors (up to 50)
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Wu Y., Huang K. H., Shin C. C., Wu T. C. Palladium‐Catalyzed Formation of Highly Substituted Naphthalenes from Arene and Alkyne Hydrocarbons // Chemistry - A European Journal. 2008. Vol. 14. No. 22. pp. 6697-6703.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/chem.200800538
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.200800538
TI - Palladium‐Catalyzed Formation of Highly Substituted Naphthalenes from Arene and Alkyne Hydrocarbons
T2 - Chemistry - A European Journal
AU - Wu, Yao-Ting
AU - Huang, Ke Hsin
AU - Shin, Chien Chueh
AU - Wu, Tsun Cheng
PY - 2008
DA - 2008/07/21
PB - Wiley
SP - 6697-6703
IS - 22
VL - 14
PMID - 18551492
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2008_Wu,
author = {Yao-Ting Wu and Ke Hsin Huang and Chien Chueh Shin and Tsun Cheng Wu},
title = {Palladium‐Catalyzed Formation of Highly Substituted Naphthalenes from Arene and Alkyne Hydrocarbons},
journal = {Chemistry - A European Journal},
year = {2008},
volume = {14},
publisher = {Wiley},
month = {jul},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.200800538},
number = {22},
pages = {6697--6703},
doi = {10.1002/chem.200800538}
}
Cite this
MLA
Copy
Wu, Yao-Ting, et al. “Palladium‐Catalyzed Formation of Highly Substituted Naphthalenes from Arene and Alkyne Hydrocarbons.” Chemistry - A European Journal, vol. 14, no. 22, Jul. 2008, pp. 6697-6703. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.200800538.