Angewandte Chemie - International Edition, volume 61, issue 35
Synthesis of Cyclopentene Derivatives via Electrochemically Induced Intermolecular Selective (3+2) Annulation
Publication type: Journal Article
Publication date: 2022-07-21
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
Cyclopentenes are common cores in many natural products, and in bioactive and functional molecules. However, their synthesis remains challenging in terms of harsh conditions, poor selectivity, prefunctionalization of the substrates, over-reliance on volatile activating reagents and the use of noble metals. Herein, we develop an electrochemical mediator-induced intermolecular selective (3+2) annulation of readily available alkenes and alkynes/alkenes, which provides a simple and efficient method for the synthesis of a library of decorated cyclopentenes and cyclopentanes. This protocol features high efficiency, mild reaction conditions, broad substrate scope, good functional group tolerance, and high regioselectivity. Potential applications are demonstrated by gram-scale synthesis as well as the construction of structural diversity and complexity. A preliminary mechanistic investigation was performed, which indicated that an iodine radical and carbon radicals are involved in this transformation.
Citations by journals
|
1
2
|
|
|
Journal of Organic Chemistry
2 publications, 22.22%
|
|
|
Nature Synthesis
1 publication, 11.11%
|
|
|
Chemical Communications
1 publication, 11.11%
|
|
|
Trends in Chemistry
1 publication, 11.11%
|
|
|
ACS Sustainable Chemistry and Engineering
1 publication, 11.11%
|
|
|
Current Opinion in Electrochemistry
1 publication, 11.11%
|
|
|
Green Chemistry
1 publication, 11.11%
|
|
|
Organic Chemistry Frontiers
1 publication, 11.11%
|
|
|
1
2
|
Citations by publishers
|
1
2
3
|
|
|
American Chemical Society (ACS)
3 publications, 33.33%
|
|
|
Royal Society of Chemistry (RSC)
3 publications, 33.33%
|
|
|
Elsevier
2 publications, 22.22%
|
|
|
Springer Nature
1 publication, 11.11%
|
|
|
1
2
3
|
- We do not take into account publications that 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":[2023,2024],"ids":[0,0],"codes":[0,0],"imageUrls":["",""],"datasets":[{"label":"Citations number","data":[6,3],"backgroundColor":["#3B82F6","#3B82F6"],"percentage":["66.67","33.33"],"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":["Journal of Organic Chemistry","Nature Synthesis","Chemical Communications","Trends in Chemistry","ACS Sustainable Chemistry and Engineering","Current Opinion in Electrochemistry","Green Chemistry","Organic Chemistry Frontiers"],"ids":[8697,29156,9073,4660,18886,13797,1017,3991],"codes":[0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[2,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[22.22,11.11,11.11,11.11,11.11,11.11,11.11,11.11],"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":["American Chemical Society (ACS)","Royal Society of Chemistry (RSC)","Elsevier","Springer Nature"],"ids":[40,123,17,8],"codes":[0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp"],"datasets":[{"label":"","data":[3,3,2,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[33.33,33.33,22.22,11.11],"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"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex
Cite this
GOST
Copy
Guan Z. et al. Synthesis of Cyclopentene Derivatives via Electrochemically Induced Intermolecular Selective (3+2) Annulation // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 35.
GOST all authors (up to 50)
Copy
Guan Z., Zhu S., Ye Y., Li X., Liu Y., Wang P., Zhang H., Huang Z., Lei A. Synthesis of Cyclopentene Derivatives via Electrochemically Induced Intermolecular Selective (3+2) Annulation // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 35.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/anie.202207059
UR - https://doi.org/10.1002/anie.202207059
TI - Synthesis of Cyclopentene Derivatives via Electrochemically Induced Intermolecular Selective (3+2) Annulation
T2 - Angewandte Chemie - International Edition
AU - Guan, Zhipeng
AU - Zhu, Shuxiang
AU - Ye, Yayu
AU - Li, Xiangwei
AU - Wang, Pengjie
AU - Huang, Zhiliang
AU - Lei, Aiwen
AU - Liu, Yanlong
AU - Zhang, Heng
PY - 2022
DA - 2022/07/21 00:00:00
PB - Wiley
IS - 35
VL - 61
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex
Copy
@article{2022_Guan,
author = {Zhipeng Guan and Shuxiang Zhu and Yayu Ye and Xiangwei Li and Pengjie Wang and Zhiliang Huang and Aiwen Lei and Yanlong Liu and Heng Zhang},
title = {Synthesis of Cyclopentene Derivatives via Electrochemically Induced Intermolecular Selective (3+2) Annulation},
journal = {Angewandte Chemie - International Edition},
year = {2022},
volume = {61},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/anie.202207059},
number = {35},
doi = {10.1002/anie.202207059}
}