Modular synthesis of 3-substituted isocoumarins via silver-catalyzed aerobic oxidation/6-endo heterocyclization of ortho-alkynylbenzaldehydes
Hao Wu
1
,
Yi-Chun Wang
1, 2, 3, 4, 5, 6
,
Andrey Shatskiy
7, 8, 9, 10, 11
,
Qiu-Yan Li
1, 2, 3, 4, 5, 6
,
Jian Quan Liu
1, 2, 3, 4, 5, 6, 7
,
Markus D Kärkäs
7, 8, 9, 10, 11
,
Xiangshan Wang
1, 2, 3, 4, 5, 6
2
School of Chemistry and Materials Science
3
Jiangsu Key Laboratory of Green Synthesis for Functional Materials
5
Xuzhou
|
6
CHINA
|
8
DEPARTMENT OF CHEMISTRY
10
SE-100 44 Stockholm
|
11
SWEDEN
|
Publication type: Journal Article
Publication date: 2021-07-13
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
34271583
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A method involving silver-catalyzed aerobic oxidation/6-endo heterocyclization of ortho-alkynylbenzaldehydes to yield 3-substituted isocoumarins is described. The developed protocol allows convenient access to a range of synthetically useful 3-substituted isocoumarins and related fused heterocyclolactones in good to high yields, using silver tetrafluoroborate as the catalyst, and atmospheric oxygen as the terminal oxidant and the source of endocyclic oxygen. Mechanistic studies suggest the involvement of a free-radical pathway.
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14
Total citations:
14
Citations from 2024:
7
(50%)
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GOST
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Wu H. et al. Modular synthesis of 3-substituted isocoumarins via silver-catalyzed aerobic oxidation/6-endo heterocyclization of ortho-alkynylbenzaldehydes // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 30. pp. 6657-6664.
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Wu H., Wang Y., Shatskiy A., Li Q., Liu J. Q., Kärkäs M. D., Wang X. Modular synthesis of 3-substituted isocoumarins via silver-catalyzed aerobic oxidation/6-endo heterocyclization of ortho-alkynylbenzaldehydes // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 30. pp. 6657-6664.
Cite this
RIS
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TY - JOUR
DO - 10.1039/d1ob01065d
UR - https://xlink.rsc.org/?DOI=D1OB01065D
TI - Modular synthesis of 3-substituted isocoumarins via silver-catalyzed aerobic oxidation/6-endo heterocyclization of ortho-alkynylbenzaldehydes
T2 - Organic and Biomolecular Chemistry
AU - Wu, Hao
AU - Wang, Yi-Chun
AU - Shatskiy, Andrey
AU - Li, Qiu-Yan
AU - Liu, Jian Quan
AU - Kärkäs, Markus D
AU - Wang, Xiangshan
PY - 2021
DA - 2021/07/13
PB - Royal Society of Chemistry (RSC)
SP - 6657-6664
IS - 30
VL - 19
PMID - 34271583
SN - 1477-0520
SN - 1477-0539
ER -
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BibTex (up to 50 authors)
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@article{2021_Wu,
author = {Hao Wu and Yi-Chun Wang and Andrey Shatskiy and Qiu-Yan Li and Jian Quan Liu and Markus D Kärkäs and Xiangshan Wang},
title = {Modular synthesis of 3-substituted isocoumarins via silver-catalyzed aerobic oxidation/6-endo heterocyclization of ortho-alkynylbenzaldehydes},
journal = {Organic and Biomolecular Chemistry},
year = {2021},
volume = {19},
publisher = {Royal Society of Chemistry (RSC)},
month = {jul},
url = {https://xlink.rsc.org/?DOI=D1OB01065D},
number = {30},
pages = {6657--6664},
doi = {10.1039/d1ob01065d}
}
Cite this
MLA
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Wu, Hao, et al. “Modular synthesis of 3-substituted isocoumarins via silver-catalyzed aerobic oxidation/6-endo heterocyclization of ortho-alkynylbenzaldehydes.” Organic and Biomolecular Chemistry, vol. 19, no. 30, Jul. 2021, pp. 6657-6664. https://xlink.rsc.org/?DOI=D1OB01065D.