Angewandte Chemie - International Edition, volume 57, issue 32, pages 10293-10298
Three-Component Gallium(III)-Promoted Addition of Halide Anions and Acetylenes to Donor-Acceptor Cyclopropanes
Publication type: Journal Article
Publication date: 2018-07-17
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
A new strategy for the three-component addition of halide anions and acetylenes to donor-acceptor cyclopropanes (DACs) is presented. This reaction, which occurs with high E selectivity, is promoted by gallium(III) salts and based on the 1,2-zwitterionic reactivity of DACs. It opens up a new group of processes involving DACs. The reaction occurs readily with a broad range of substrates and is tolerant of various functional groups. This methodology makes it possible to assemble highly functionalized vinyl halides, which are very convenient building blocks in organic synthesis. A possible mechanism of this reaction and its stereochemical aspects are discussed in detail.
Top-30
Citations by journals
|
1
2
3
4
5
6
7
8
|
|
|
Journal of Organic Chemistry
8 publications, 18.18%
|
|
|
Organic Letters
4 publications, 9.09%
|
|
|
Russian Chemical Bulletin
4 publications, 9.09%
|
|
|
Mendeleev Communications
3 publications, 6.82%
|
|
|
Tetrahedron Letters
3 publications, 6.82%
|
|
|
Organic and Biomolecular Chemistry
2 publications, 4.55%
|
|
|
Molecules
2 publications, 4.55%
|
|
|
Angewandte Chemie
2 publications, 4.55%
|
|
|
Angewandte Chemie - International Edition
2 publications, 4.55%
|
|
|
Organometallics
1 publication, 2.27%
|
|
|
Chemical Record
1 publication, 2.27%
|
|
|
European Journal of Organic Chemistry
1 publication, 2.27%
|
|
|
ChemCatChem
1 publication, 2.27%
|
|
|
Asian Journal of Organic Chemistry
1 publication, 2.27%
|
|
|
ChemistrySelect
1 publication, 2.27%
|
|
|
Journal of the American Chemical Society
1 publication, 2.27%
|
|
|
Chemical Communications
1 publication, 2.27%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 2.27%
|
|
|
Synlett
1 publication, 2.27%
|
|
|
Molecular Catalysis
1 publication, 2.27%
|
|
|
Russian Chemical Reviews
1 publication, 2.27%
|
|
|
Nature Communications
1 publication, 2.27%
|
|
|
1
2
3
4
5
6
7
8
|
Citations by publishers
|
2
4
6
8
10
12
14
|
|
|
American Chemical Society (ACS)
14 publications, 31.82%
|
|
|
Wiley
10 publications, 22.73%
|
|
|
Elsevier
8 publications, 18.18%
|
|
|
Springer Nature
5 publications, 11.36%
|
|
|
Royal Society of Chemistry (RSC)
3 publications, 6.82%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 4.55%
|
|
|
Thieme
1 publication, 2.27%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 2.27%
|
|
|
2
4
6
8
10
12
14
|
- 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":[2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0],"imageUrls":["","","","","","",""],"datasets":[{"label":"Citations number","data":[5,8,7,9,6,4,5],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["11.36","18.18","15.91","20.45","13.64","9.09","11.36"],"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","Organic Letters","Russian Chemical Bulletin","Mendeleev Communications","Tetrahedron Letters","Organic and Biomolecular Chemistry","Molecules","Angewandte Chemie","Angewandte Chemie - International Edition","Organometallics","Chemical Record","European Journal of Organic Chemistry","ChemCatChem","Asian Journal of Organic Chemistry","ChemistrySelect","Journal of the American Chemical Society","Chemical Communications","Advanced Synthesis and Catalysis","Synlett","Molecular Catalysis","Russian Chemical Reviews","Nature Communications"],"ids":[8697,3315,10918,5294,6133,541,1770,25450,19215,1409,22413,19472,10149,9409,8021,4813,9073,3906,10217,4906,23802,3231],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp"],"datasets":[{"label":"","data":[8,4,4,3,3,2,2,2,2,1,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[18.18,9.09,9.09,6.82,6.82,4.55,4.55,4.55,4.55,2.27,2.27,2.27,2.27,2.27,2.27,2.27,2.27,2.27,2.27,2.27,2.27,2.27],"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)","Wiley","Elsevier","Springer Nature","Royal Society of Chemistry (RSC)","Multidisciplinary Digital Publishing Institute (MDPI)","Thieme","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[40,11,17,8,123,202,135,9422],"codes":[0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[14,10,8,5,3,2,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[31.82,22.73,18.18,11.36,6.82,4.55,2.27,2.27],"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":[2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,3,1,3,1,1,1],"percentage":["0","6.82","2.27","6.82","2.27","2.27","2.27"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,2,2,0,0,1,0],"percentage":["0","4.55","4.55","0","0","2.27","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[5,3,4,6,4,2,4],"percentage":["11.36","6.82","9.09","13.64","9.09","4.55","9.09"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,0,0,1,0,0],"percentage":["0","0","0","0","2.27","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":[2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,3,3,3,1,1,1],"percentage":["0","6.82","6.82","6.82","2.27","2.27","2.27"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,3,2,1,3,1,0],"percentage":["0","6.82","4.55","2.27","6.82","2.27","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[4,2,2,5,1,2,3],"percentage":["9.09","4.55","4.55","11.36","2.27","4.55","6.82"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,0,0,0,1,0,1],"percentage":["2.27","0","0","0","2.27","0","2.27"]}]},"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
Novikov R. G. et al. Three-Component Gallium(III)-Promoted Addition of Halide Anions and Acetylenes to Donor-Acceptor Cyclopropanes // Angewandte Chemie - International Edition. 2018. Vol. 57. No. 32. pp. 10293-10298.
GOST all authors (up to 50)
Copy
Novikov R. G., Borisov D. D., Tarasova A. V., Tkachev Y. V., Tomilov Y. V. Three-Component Gallium(III)-Promoted Addition of Halide Anions and Acetylenes to Donor-Acceptor Cyclopropanes // Angewandte Chemie - International Edition. 2018. Vol. 57. No. 32. pp. 10293-10298.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/anie.201803541
UR - https://doi.org/10.1002/anie.201803541
TI - Three-Component Gallium(III)-Promoted Addition of Halide Anions and Acetylenes to Donor-Acceptor Cyclopropanes
T2 - Angewandte Chemie - International Edition
AU - Borisov, Denis D
AU - Tarasova, Anna V
AU - Novikov, Roman G.
AU - Tomilov, Yury V.
AU - Tkachev, Yaroslav V.
PY - 2018
DA - 2018/07/17 00:00:00
PB - Wiley
SP - 10293-10298
IS - 32
VL - 57
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex
Copy
@article{2018_Novikov,
author = {Denis D Borisov and Anna V Tarasova and Roman G. Novikov and Yury V. Tomilov and Yaroslav V. Tkachev},
title = {Three-Component Gallium(III)-Promoted Addition of Halide Anions and Acetylenes to Donor-Acceptor Cyclopropanes},
journal = {Angewandte Chemie - International Edition},
year = {2018},
volume = {57},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/anie.201803541},
number = {32},
pages = {10293--10298},
doi = {10.1002/anie.201803541}
}
Cite this
MLA
Copy
Novikov, Roman G., et al. “Three-Component Gallium(III)-Promoted Addition of Halide Anions and Acetylenes to Donor-Acceptor Cyclopropanes.” Angewandte Chemie - International Edition, vol. 57, no. 32, Jul. 2018, pp. 10293-10298. https://doi.org/10.1002/anie.201803541.
Profiles