Accounts of Chemical Research, volume 47, issue 3, pages 913-924
Gold-catalyzed tandem reactions of methylenecyclopropanes and vinylidenecyclopropanes.
Publication type: Journal Article
Publication date: 2013-10-30
Journal:
Accounts of Chemical Research
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 18.3
ISSN: 00014842, 15204898
General Chemistry
General Medicine
Abstract
Gold catalysis is often the key step in the synthesis of natural products, and is a powerful tool for tandem or domino reaction processes. Both gold salts and complexes are among the most powerful soft Lewis acids for electrophilic activation of carbon-carbon multiple bonds toward a variety of nucleophiles. The core of these reactions relies on the interaction between gold catalysts and π-bonds of alkenes, alkynes, and allenes. Activation of functional groups by gold complexes provides a useful and important method for facilitating many different organic transformations with high atom efficiency. Although they are highly strained, methylenecyclopropanes (MCPs) and vinylidenecyclopropanes (VDCPs) are readily accessible molecules that have served as useful building blocks in organic synthesis. Because of their unique structural and electronic properties, significant developments have been made in the presence of transition metal catalysts such as nickel, rhodium, palladium, and ruthenium during the past decades. However, less attention has been paid to the gold-catalyzed chemistry of MCPs and VDCPs. In this Account, we describe gold-catalyzed chemical transformations of MCPs and VDCPs developed both in our laboratory and by other researchers. Chemists have demonstrated that MCPs and VDCPs have amphiphilic properties. When MCPs or VDCPs are activated by a gold catalyst, subsequent nucleophilic attack by other reagents or ring-opening (ring-expansion) of the cyclopropane moiety will occur. However, the C-C double bonds of MCPs and VDCPs can also serve as nucleophilic reagents while more electrophilic reagents are present and activated by gold catalyst, and then further cascade reactions take place as triggered by the release of ring strain of cyclopropane. Based on this strategy, both our group and others have found some interesting gold-catalyzed transformations in recent years. These transformations of MCPs and VDCPs can produce a variety of polycyclic and heterocyclic structures, containing different sized skeletons. Moreover, we have carried out some isotopic labeling experiments and computational studies for mechanistic investigation. These reactions always give the desired products with high level control of chemo-, regio-, and diastereoselectivities, making them highly valuable for the synthesis of natural products and to the pharmaceutical industry and medicine in general.
Top-30
Citations by journals
|
5
10
15
20
25
30
35
|
|
|
Organic Letters
31 publications, 10.37%
|
|
|
Advanced Synthesis and Catalysis
29 publications, 9.7%
|
|
|
Organic Chemistry Frontiers
25 publications, 8.36%
|
|
|
Chemistry - A European Journal
23 publications, 7.69%
|
|
|
Angewandte Chemie
18 publications, 6.02%
|
|
|
Angewandte Chemie - International Edition
18 publications, 6.02%
|
|
|
Chemical Communications
17 publications, 5.69%
|
|
|
Journal of Organic Chemistry
16 publications, 5.35%
|
|
|
Organic and Biomolecular Chemistry
12 publications, 4.01%
|
|
|
Chemical Science
9 publications, 3.01%
|
|
|
European Journal of Organic Chemistry
7 publications, 2.34%
|
|
|
ACS Catalysis
7 publications, 2.34%
|
|
|
Asian Journal of Organic Chemistry
5 publications, 1.67%
|
|
|
ChemCatChem
5 publications, 1.67%
|
|
|
Chemical Reviews
5 publications, 1.67%
|
|
|
Organometallics
4 publications, 1.34%
|
|
|
Chemical Society Reviews
4 publications, 1.34%
|
|
|
Tetrahedron
3 publications, 1%
|
|
|
Tetrahedron Letters
3 publications, 1%
|
|
|
Journal of Organometallic Chemistry
3 publications, 1%
|
|
|
Chemistry - An Asian Journal
3 publications, 1%
|
|
|
Journal of the American Chemical Society
3 publications, 1%
|
|
|
Russian Chemical Reviews
2 publications, 0.67%
|
|
|
Molecules
2 publications, 0.67%
|
|
|
Coordination Chemistry Reviews
2 publications, 0.67%
|
|
|
Chemical Record
2 publications, 0.67%
|
|
|
ChemistrySelect
2 publications, 0.67%
|
|
|
Chinese Journal of Chemistry
2 publications, 0.67%
|
|
|
Green Chemistry
2 publications, 0.67%
|
|
|
5
10
15
20
25
30
35
|
Citations by publishers
|
20
40
60
80
100
120
140
|
|
|
Wiley
121 publications, 40.47%
|
|
|
Royal Society of Chemistry (RSC)
76 publications, 25.42%
|
|
|
American Chemical Society (ACS)
67 publications, 22.41%
|
|
|
Elsevier
14 publications, 4.68%
|
|
|
Springer Nature
5 publications, 1.67%
|
|
|
Thieme
4 publications, 1.34%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
3 publications, 1%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
2 publications, 0.67%
|
|
|
Beilstein-Institut
1 publication, 0.33%
|
|
|
Shanghai Institute of Organic Chemistry
1 publication, 0.33%
|
|
|
Taylor & Francis
1 publication, 0.33%
|
|
|
The Japan Institute of Heterocyclic Chemistry
1 publication, 0.33%
|
|
|
20
40
60
80
100
120
140
|
- 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":[2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["","","","","","","","","","",""],"datasets":[{"label":"Citations number","data":[20,43,47,28,36,41,25,23,18,11,7],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["6.69","14.38","15.72","9.36","12.04","13.71","8.36","7.69","6.02","3.68","2.34"],"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":["Organic Letters","Advanced Synthesis and Catalysis","Organic Chemistry Frontiers","Chemistry - A European Journal","Angewandte Chemie","Angewandte Chemie - International Edition","Chemical Communications","Journal of Organic Chemistry","Organic and Biomolecular Chemistry","Chemical Science","European Journal of Organic Chemistry","ACS Catalysis","Asian Journal of Organic Chemistry","ChemCatChem","Chemical Reviews","Organometallics","Chemical Society Reviews","Tetrahedron","Tetrahedron Letters","Journal of Organometallic Chemistry","Chemistry - An Asian Journal","Journal of the American Chemical Society","Russian Chemical Reviews","Molecules","Coordination Chemistry Reviews","Chemical Record","ChemistrySelect","Chinese Journal of Chemistry","Green Chemistry"],"ids":[3315,3906,3991,24708,25450,19215,9073,8697,541,9646,19472,4873,9409,10149,13718,1409,20586,3439,6133,11834,10120,4813,23802,1770,13437,22413,8021,7222,1017],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_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\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[31,29,25,23,18,18,17,16,12,9,7,7,5,5,5,4,4,3,3,3,3,3,2,2,2,2,2,2,2],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[10.37,9.7,8.36,7.69,6.02,6.02,5.69,5.35,4.01,3.01,2.34,2.34,1.67,1.67,1.67,1.34,1.34,1,1,1,1,1,0.67,0.67,0.67,0.67,0.67,0.67,0.67],"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":["Wiley","Royal Society of Chemistry (RSC)","American Chemical Society (ACS)","Elsevier","Springer Nature","Thieme","Multidisciplinary Digital Publishing Institute (MDPI)","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii","Beilstein-Institut","Shanghai Institute of Organic Chemistry","Taylor & Francis","The Japan Institute of Heterocyclic Chemistry"],"ids":[11,123,40,17,8,135,202,9422,6139,8960,18,9411],"codes":[0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/ex6KJoZujZOZFZh7jGfeHauiftuB3CI7iwJVFRDg_medium.webp","\/storage\/images\/resized\/6EJSsoiR4fNMNMPFBpMh5yKuYKcPXJDQKvKVeEMy_medium.webp","\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp","\/storage\/images\/resized\/SovkqI6gX6to8o5XBnS9RNxEOYVicn7hatkMzrvl_medium.webp"],"datasets":[{"label":"","data":[121,76,67,14,5,4,3,2,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[40.47,25.42,22.41,4.68,1.67,1.34,1,0.67,0.33,0.33,0.33,0.33],"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":[2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0,0,1,0,0,0],"percentage":["0","0","0","0","0","0","0","0.33","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,4,0,1,0,2,0,0,2,0,0],"percentage":["0","1.34","0","0.33","0","0.67","0","0","0.67","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[3,6,5,3,1,3,2,1,1,2,0],"percentage":["1","2.01","1.67","1","0.33","1","0.67","0.33","0.33","0.67","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[15,32,42,23,34,36,22,20,15,9,7],"percentage":["5.02","10.7","14.05","7.69","11.37","12.04","7.36","6.69","5.02","3.01","2.34"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[2,1,0,1,1,0,1,1,0,0,0],"percentage":["0.67","0.33","0","0.33","0.33","0","0.33","0.33","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":[2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,1,0,0,0,0,0,1,0,0,0],"percentage":["0","0.33","0","0","0","0","0","0.33","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[3,5,1,1,0,1,0,0,2,1,0],"percentage":["1","1.67","0.33","0.33","0","0.33","0","0","0.67","0.33","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[3,13,22,11,8,8,8,9,5,2,3],"percentage":["1","4.35","7.36","3.68","2.68","2.68","2.68","3.01","1.67","0.67","1"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[9,18,22,14,25,31,14,12,10,7,4],"percentage":["3.01","6.02","7.36","4.68","8.36","10.37","4.68","4.01","3.34","2.34","1.34"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[5,6,2,2,3,1,3,1,1,1,0],"percentage":["1.67","2.01","0.67","0.67","1","0.33","1","0.33","0.33","0.33","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
Zhang D. H., Tang X., Shi M. Gold-catalyzed tandem reactions of methylenecyclopropanes and vinylidenecyclopropanes. // Accounts of Chemical Research. 2013. Vol. 47. No. 3. pp. 913-924.
GOST all authors (up to 50)
Copy
Zhang D. H., Tang X., Shi M. Gold-catalyzed tandem reactions of methylenecyclopropanes and vinylidenecyclopropanes. // Accounts of Chemical Research. 2013. Vol. 47. No. 3. pp. 913-924.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ar400159r
UR - https://doi.org/10.1021/ar400159r
TI - Gold-catalyzed tandem reactions of methylenecyclopropanes and vinylidenecyclopropanes.
T2 - Accounts of Chemical Research
AU - Zhang, Di Han
AU - Tang, Xiang-Ying
AU - Shi, Min
PY - 2013
DA - 2013/10/30 00:00:00
PB - American Chemical Society (ACS)
SP - 913-924
IS - 3
VL - 47
SN - 0001-4842
SN - 1520-4898
ER -
Cite this
BibTex
Copy
@article{2013_Zhang,
author = {Di Han Zhang and Xiang-Ying Tang and Min Shi},
title = {Gold-catalyzed tandem reactions of methylenecyclopropanes and vinylidenecyclopropanes.},
journal = {Accounts of Chemical Research},
year = {2013},
volume = {47},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/ar400159r},
number = {3},
pages = {913--924},
doi = {10.1021/ar400159r}
}
Cite this
MLA
Copy
Zhang, Di Han, et al. “Gold-catalyzed tandem reactions of methylenecyclopropanes and vinylidenecyclopropanes..” Accounts of Chemical Research, vol. 47, no. 3, Oct. 2013, pp. 913-924. https://doi.org/10.1021/ar400159r.