Journal of Organic Chemistry, volume 85, issue 10, pages 6359-6371
Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives
Publication type: Journal Article
Publication date: 2020-04-17
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
The first metal-free and facile radical addition/cyclization of simple alcohols with diaryl(arylethynyl)phosphine oxides has been described with azobisisobutyronitrile as a radical initiator, affording an efficient and one-pot procedure to access a new class of hydroxymethyl benzo[b]phosphole oxides and 6H-indeno[2,1-b]phosphindole 5-oxides for potential application in organic materials via sequential C(sp3)-H/C(sp2)-H functionalization. The method employs easily accessible starting materials and is endowed with high regioselectivity and broad functional-group tolerance.
Top-30
Citations by journals
|
1
2
|
|
|
Chemistry - A European Journal
2 publications, 16.67%
|
|
|
European Journal of Organic Chemistry
2 publications, 16.67%
|
|
|
Tetrahedron Letters
1 publication, 8.33%
|
|
|
Organic Letters
1 publication, 8.33%
|
|
|
Journal of Organic Chemistry
1 publication, 8.33%
|
|
|
Dalton Transactions
1 publication, 8.33%
|
|
|
Organic Chemistry Frontiers
1 publication, 8.33%
|
|
|
Russian Chemical Reviews
1 publication, 8.33%
|
|
|
Chemical Record
1 publication, 8.33%
|
|
|
1
2
|
Citations by publishers
|
1
2
3
4
5
6
|
|
|
Wiley
6 publications, 50%
|
|
|
American Chemical Society (ACS)
2 publications, 16.67%
|
|
|
Royal Society of Chemistry (RSC)
2 publications, 16.67%
|
|
|
Elsevier
1 publication, 8.33%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 8.33%
|
|
|
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":[2020,2021,2022,2023,2024],"ids":[0,0,0,0,0],"codes":[0,0,0,0,0],"imageUrls":["","","","",""],"datasets":[{"label":"Citations number","data":[2,3,4,1,2],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["16.67","25","33.33","8.33","16.67"],"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":["Chemistry - A European Journal","European Journal of Organic Chemistry","Tetrahedron Letters","Organic Letters","Journal of Organic Chemistry","Dalton Transactions","Organic Chemistry Frontiers","Russian Chemical Reviews","Chemical Record"],"ids":[24708,19472,6133,3315,8697,8473,3991,23802,22413],"codes":[0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_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\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp"],"datasets":[{"label":"","data":[2,2,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[16.67,16.67,8.33,8.33,8.33,8.33,8.33,8.33,8.33],"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":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Wiley","American Chemical Society (ACS)","Royal Society of Chemistry (RSC)","Elsevier","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[11,40,123,17,9422],"codes":[0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[6,2,2,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[50,16.67,16.67,8.33,8.33],"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":[2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0],"percentage":["0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,1,0,0],"percentage":["0","0","8.33","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,0,1,1,0],"percentage":["0","0","8.33","8.33","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[2,3,1,0,2],"percentage":["16.67","25","8.33","0","16.67"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,1,0,0],"percentage":["0","0","8.33","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":[2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0],"percentage":["0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,1,0,0],"percentage":["0","0","8.33","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,2,1,1,0],"percentage":["0","16.67","8.33","8.33","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[2,1,1,0,2],"percentage":["16.67","8.33","8.33","0","16.67"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,1,0,0],"percentage":["0","0","8.33","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
Guo J. et al. Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives // Journal of Organic Chemistry. 2020. Vol. 85. No. 10. pp. 6359-6371.
GOST all authors (up to 50)
Copy
Guo J., Mao C., Deng B., Ye L., Yin Y., Gao Y., Tu S. Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives // Journal of Organic Chemistry. 2020. Vol. 85. No. 10. pp. 6359-6371.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.0c00118
UR - https://doi.org/10.1021/acs.joc.0c00118
TI - Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives
T2 - Journal of Organic Chemistry
AU - Guo, Jiami
AU - Mao, Chenlu
AU - Ye, Liyi
AU - Yin, Yingwu
AU - Gao, Yu-Xing
AU - Deng, Bin
AU - Tu, Song
PY - 2020
DA - 2020/04/17 00:00:00
PB - American Chemical Society (ACS)
SP - 6359-6371
IS - 10
VL - 85
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex
Copy
@article{2020_Guo,
author = {Jiami Guo and Chenlu Mao and Liyi Ye and Yingwu Yin and Yu-Xing Gao and Bin Deng and Song Tu},
title = {Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.joc.0c00118},
number = {10},
pages = {6359--6371},
doi = {10.1021/acs.joc.0c00118}
}
Cite this
MLA
Copy
Guo, Jiami, et al. “Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives.” Journal of Organic Chemistry, vol. 85, no. 10, Apr. 2020, pp. 6359-6371. https://doi.org/10.1021/acs.joc.0c00118.