Journal of Organic Chemistry, volume 84, issue 16, pages 9984-9994
Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids
Publication type: Journal Article
Publication date: 2019-07-18
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
A novel and efficient AgNO3-facilitated oxidative C-C σ-bond difunctionalization of alkylidenecyclopropanes with α-ketoacids for preparing 2-acyl-substituted 3,4-dihydronaphthalenes is developed. This radical acylation/arylation transformation proceeds via decarboxylation of the α-ketoacid, acylation of the carbon-carbon double bond, cleavage of the carbon-carbon σ-bond, and cyclization with a connected aromatic ring and offers a mild and facile strategy for acylation/arylation of carbon-carbon σ-bonds with an acyl radical and an aromatic ring to build two new carbon-carbon bonds. This method uses an inexpensive oxidant, features a wide substrate scope, and is operationally simple.
Top-30
Citations by journals
|
1
2
|
|
|
Asian Journal of Organic Chemistry
2 publications, 11.11%
|
|
|
Journal of Organic Chemistry
2 publications, 11.11%
|
|
|
Organic Letters
2 publications, 11.11%
|
|
|
Chemical Communications
2 publications, 11.11%
|
|
|
Organic and Biomolecular Chemistry
2 publications, 11.11%
|
|
|
Organic Chemistry Frontiers
2 publications, 11.11%
|
|
|
Chinese Journal of Organic Chemistry
1 publication, 5.56%
|
|
|
Journal of Environmental Chemical Engineering
1 publication, 5.56%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 5.56%
|
|
|
Chemistry - An Asian Journal
1 publication, 5.56%
|
|
|
Russian Chemical Reviews
1 publication, 5.56%
|
|
|
ACS Catalysis
1 publication, 5.56%
|
|
|
1
2
|
Citations by publishers
|
1
2
3
4
5
6
|
|
|
Royal Society of Chemistry (RSC)
6 publications, 33.33%
|
|
|
American Chemical Society (ACS)
5 publications, 27.78%
|
|
|
Wiley
4 publications, 22.22%
|
|
|
Shanghai Institute of Organic Chemistry
1 publication, 5.56%
|
|
|
Elsevier
1 publication, 5.56%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 5.56%
|
|
|
1
2
3
4
5
6
|
- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0],"codes":[0,0,0,0,0,0],"imageUrls":["","","","","",""],"datasets":[{"label":"Citations number","data":[1,3,5,4,1,4],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["5.56","16.67","27.78","22.22","5.56","22.22"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Asian Journal of Organic Chemistry","Journal of Organic Chemistry","Organic Letters","Chemical Communications","Organic and Biomolecular Chemistry","Organic Chemistry Frontiers","Chinese Journal of Organic Chemistry","Journal of Environmental Chemical Engineering","Advanced Synthesis and Catalysis","Chemistry - An Asian Journal","Russian Chemical Reviews","ACS Catalysis"],"ids":[9409,8697,3315,9073,541,3991,11696,240,3906,10120,23802,4873],"codes":[0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/6EJSsoiR4fNMNMPFBpMh5yKuYKcPXJDQKvKVeEMy_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp"],"datasets":[{"label":"","data":[2,2,2,2,2,2,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[11.11,11.11,11.11,11.11,11.11,11.11,5.56,5.56,5.56,5.56,5.56,5.56],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Royal Society of Chemistry (RSC)","American Chemical Society (ACS)","Wiley","Shanghai Institute of Organic Chemistry","Elsevier","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[123,40,11,8960,17,9422],"codes":[0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/6EJSsoiR4fNMNMPFBpMh5yKuYKcPXJDQKvKVeEMy_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[6,5,4,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[33.33,27.78,22.22,5.56,5.56,5.56],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0],"percentage":["0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0,1,0,0],"percentage":["0","0","0","5.56","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,0,1,0,0,1],"percentage":["0","0","5.56","0","0","5.56"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,3,4,3,1,3],"percentage":["5.56","16.67","22.22","16.67","5.56","16.67"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,0,0,0,0],"percentage":["0","0","0","0","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0],"percentage":["0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0,1,0,0],"percentage":["0","0","0","5.56","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,1,3,0,1,1],"percentage":["5.56","5.56","16.67","0","5.56","5.56"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[0,2,2,3,0,3],"percentage":["0","11.11","11.11","16.67","0","16.67"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,0,0,0,0],"percentage":["0","0","0","0","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Liu Yu. et al. Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids // Journal of Organic Chemistry. 2019. Vol. 84. No. 16. pp. 9984-9994.
GOST all authors (up to 50)
Copy
Liu Yu., Chen Z., Wang Q., Zhou C., Xiong B., Yang C. A., Tang K. Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids // Journal of Organic Chemistry. 2019. Vol. 84. No. 16. pp. 9984-9994.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.9b01125
UR - https://doi.org/10.1021/acs.joc.9b01125
TI - Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids
T2 - Journal of Organic Chemistry
AU - Chen, Zan
AU - Wang, Qiao-Lin
AU - Zhou, Cong-Shan
AU - Yang, Chang An
AU - Liu, Yu
AU - Xiong, Biquan
AU - Tang, Kewen
PY - 2019
DA - 2019/07/18 00:00:00
PB - American Chemical Society (ACS)
SP - 9984-9994
IS - 16
VL - 84
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex
Copy
@article{2019_Liu,
author = {Zan Chen and Qiao-Lin Wang and Cong-Shan Zhou and Chang An Yang and Yu Liu and Biquan Xiong and Kewen Tang},
title = {Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.joc.9b01125},
number = {16},
pages = {9984--9994},
doi = {10.1021/acs.joc.9b01125}
}
Cite this
MLA
Copy
Liu, Yu., et al. “Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids.” Journal of Organic Chemistry, vol. 84, no. 16, Jul. 2019, pp. 9984-9994. https://doi.org/10.1021/acs.joc.9b01125.