Organic Letters, volume 18, issue 9, pages 1952-1955
The Discovery of Quinoxaline-Based Metathesis Catalysts from Synthesis of Grazoprevir (MK-5172)
Michael J. Williams
1
,
Jongrock Kong
1
,
Cheol K Chung
1
,
Andrew Brunskill
1
,
Louis Charles Campeau
1
,
Mark Mclaughlin
1
1
Department of Process and
Analytical Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, United States
|
Publication type: Journal Article
Publication date: 2016-04-28
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Olefin metathesis (OM) is a reliable and practical synthetic methodology for challenging carbon-carbon bond formations. While existing catalysts can effect many of these transformations, the synthesis and development of new catalysts is essential to increase the application breadth of OM and to achieve improved catalyst activity. The unexpected initial discovery of a novel olefin metathesis catalyst derived from synthetic efforts toward the HCV therapeutic agent grazoprevir (MK-5172) is described. This initial finding has evolved into a class of tunable, shelf-stable ruthenium OM catalysts that are easily prepared and exhibit unique catalytic activity.
Top-30
Citations by journals
|
1
2
3
4
|
|
|
ACS Symposium Series
4 publications, 17.39%
|
|
|
Synthesis
3 publications, 13.04%
|
|
|
Bioorganic and Medicinal Chemistry Letters
1 publication, 4.35%
|
|
|
Coordination Chemistry Reviews
1 publication, 4.35%
|
|
|
ChemInform
1 publication, 4.35%
|
|
|
Chemistry - A European Journal
1 publication, 4.35%
|
|
|
Organic Letters
1 publication, 4.35%
|
|
|
Journal of Organic Chemistry
1 publication, 4.35%
|
|
|
ACS Catalysis
1 publication, 4.35%
|
|
|
Catalysts
1 publication, 4.35%
|
|
|
Dalton Transactions
1 publication, 4.35%
|
|
|
Topics in Medicinal Chemistry
1 publication, 4.35%
|
|
|
Topics in Organometallic Chemistry
1 publication, 4.35%
|
|
|
Russian Chemical Reviews
1 publication, 4.35%
|
|
|
1
2
3
4
|
Citations by publishers
|
1
2
3
4
5
6
7
|
|
|
American Chemical Society (ACS)
7 publications, 30.43%
|
|
|
Wiley
3 publications, 13.04%
|
|
|
Thieme
3 publications, 13.04%
|
|
|
Elsevier
2 publications, 8.7%
|
|
|
Springer Nature
2 publications, 8.7%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 4.35%
|
|
|
Royal Society of Chemistry (RSC)
1 publication, 4.35%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 4.35%
|
|
|
1
2
3
4
5
6
7
|
- 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":[2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0,0,0],"imageUrls":["","","","","","","","",""],"datasets":[{"label":"Citations number","data":[2,0,6,4,6,2,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["8.7",0,"26.09","17.39","26.09","8.7","4.35","4.35","4.35"],"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":["ACS Symposium Series","Synthesis","Bioorganic and Medicinal Chemistry Letters","Coordination Chemistry Reviews","ChemInform","Chemistry - A European Journal","Organic Letters","Journal of Organic Chemistry","ACS Catalysis","Catalysts","Dalton Transactions","Topics in Medicinal Chemistry","Topics in Organometallic Chemistry","Russian Chemical Reviews"],"ids":[23301,10934,8828,13437,25372,24708,3315,8697,4873,3739,8473,15945,23840,23802],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_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\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[4,3,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[17.39,13.04,4.35,4.35,4.35,4.35,4.35,4.35,4.35,4.35,4.35,4.35,4.35,4.35],"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","Thieme","Elsevier","Springer Nature","Multidisciplinary Digital Publishing Institute (MDPI)","Royal Society of Chemistry (RSC)","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[40,11,135,17,8,202,123,9422],"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\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[7,3,3,2,2,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[30.43,13.04,13.04,8.7,8.7,4.35,4.35,4.35],"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":[2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,4,0,0,0,0],"percentage":["0","0","0","0","17.39","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,0,0,0,0,1,0,1,0],"percentage":["0","0","0","0","0","4.35","0","4.35","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,0,5,2,1,0,0,0,1],"percentage":["4.35","0","21.74","8.7","4.35","0","0","0","4.35"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,0,1,2,1,1,1,0,0],"percentage":["4.35","0","4.35","8.7","4.35","4.35","4.35","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":[2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,0,1,2,1,1,0,1,0],"percentage":["0","0","4.35","8.7","4.35","4.35","0","4.35","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,0,4,0,0,0,0,0,1],"percentage":["4.35","0","17.39","0","0","0","0","0","4.35"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,0,1,2,5,1,1,0,0],"percentage":["4.35","0","4.35","8.7","21.74","4.35","4.35","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
Williams M. J. et al. The Discovery of Quinoxaline-Based Metathesis Catalysts from Synthesis of Grazoprevir (MK-5172) // Organic Letters. 2016. Vol. 18. No. 9. pp. 1952-1955.
GOST all authors (up to 50)
Copy
Williams M. J., Kong J., Chung C. K., Brunskill A., Campeau L. C., Mclaughlin M. The Discovery of Quinoxaline-Based Metathesis Catalysts from Synthesis of Grazoprevir (MK-5172) // Organic Letters. 2016. Vol. 18. No. 9. pp. 1952-1955.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.6b00070
UR - https://doi.org/10.1021/acs.orglett.6b00070
TI - The Discovery of Quinoxaline-Based Metathesis Catalysts from Synthesis of Grazoprevir (MK-5172)
T2 - Organic Letters
AU - Williams, Michael J.
AU - Kong, Jongrock
AU - Chung, Cheol K
AU - Brunskill, Andrew
AU - Campeau, Louis Charles
AU - Mclaughlin, Mark
PY - 2016
DA - 2016/04/28 00:00:00
PB - American Chemical Society (ACS)
SP - 1952-1955
IS - 9
VL - 18
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex
Copy
@article{2016_Williams,
author = {Michael J. Williams and Jongrock Kong and Cheol K Chung and Andrew Brunskill and Louis Charles Campeau and Mark Mclaughlin},
title = {The Discovery of Quinoxaline-Based Metathesis Catalysts from Synthesis of Grazoprevir (MK-5172)},
journal = {Organic Letters},
year = {2016},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.orglett.6b00070},
number = {9},
pages = {1952--1955},
doi = {10.1021/acs.orglett.6b00070}
}
Cite this
MLA
Copy
Williams, Michael J., et al. “The Discovery of Quinoxaline-Based Metathesis Catalysts from Synthesis of Grazoprevir (MK-5172).” Organic Letters, vol. 18, no. 9, Apr. 2016, pp. 1952-1955. https://doi.org/10.1021/acs.orglett.6b00070.