Cargando…

Visible-light-induced aerobic C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols

A novel and efficient method of visible-light-induced C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols is developed. This approach uses readily available fluoroalkyl alcohols as fluoroalkoxylation reagents and displays a wide substrate scope, providing the fluoroalkoxylated...

Descripción completa

Detalles Bibliográficos
Autores principales: Xu, Xiaobo, Xia, Chengcai, Li, Xiaojun, Sun, Jian, Hao, Liqiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9047172/
https://www.ncbi.nlm.nih.gov/pubmed/35494590
http://dx.doi.org/10.1039/c9ra10194b
_version_ 1784695674759020544
author Xu, Xiaobo
Xia, Chengcai
Li, Xiaojun
Sun, Jian
Hao, Liqiang
author_facet Xu, Xiaobo
Xia, Chengcai
Li, Xiaojun
Sun, Jian
Hao, Liqiang
author_sort Xu, Xiaobo
collection PubMed
description A novel and efficient method of visible-light-induced C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols is developed. This approach uses readily available fluoroalkyl alcohols as fluoroalkoxylation reagents and displays a wide substrate scope, providing the fluoroalkoxylated products in moderate to good yields. Compared with the previous method, such a transformation uses oxygen as an oxidant, which avoids the utilization of plenty of PhI(TFA)(2). In addition, this strategy also gives a practical tool for the rapid synthesis of histamine-4 receptor antagonist and new N-containing bidentate ligands. A radical mechanism was suggested according to the results of control experiments.
format Online
Article
Text
id pubmed-9047172
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90471722022-04-28 Visible-light-induced aerobic C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols Xu, Xiaobo Xia, Chengcai Li, Xiaojun Sun, Jian Hao, Liqiang RSC Adv Chemistry A novel and efficient method of visible-light-induced C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols is developed. This approach uses readily available fluoroalkyl alcohols as fluoroalkoxylation reagents and displays a wide substrate scope, providing the fluoroalkoxylated products in moderate to good yields. Compared with the previous method, such a transformation uses oxygen as an oxidant, which avoids the utilization of plenty of PhI(TFA)(2). In addition, this strategy also gives a practical tool for the rapid synthesis of histamine-4 receptor antagonist and new N-containing bidentate ligands. A radical mechanism was suggested according to the results of control experiments. The Royal Society of Chemistry 2020-01-09 /pmc/articles/PMC9047172/ /pubmed/35494590 http://dx.doi.org/10.1039/c9ra10194b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Xu, Xiaobo
Xia, Chengcai
Li, Xiaojun
Sun, Jian
Hao, Liqiang
Visible-light-induced aerobic C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols
title Visible-light-induced aerobic C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols
title_full Visible-light-induced aerobic C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols
title_fullStr Visible-light-induced aerobic C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols
title_full_unstemmed Visible-light-induced aerobic C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols
title_short Visible-light-induced aerobic C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols
title_sort visible-light-induced aerobic c3–h fluoroalkoxylation of quinoxalin-2(1h)-ones with fluoroalkyl alcohols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9047172/
https://www.ncbi.nlm.nih.gov/pubmed/35494590
http://dx.doi.org/10.1039/c9ra10194b
work_keys_str_mv AT xuxiaobo visiblelightinducedaerobicc3hfluoroalkoxylationofquinoxalin21honeswithfluoroalkylalcohols
AT xiachengcai visiblelightinducedaerobicc3hfluoroalkoxylationofquinoxalin21honeswithfluoroalkylalcohols
AT lixiaojun visiblelightinducedaerobicc3hfluoroalkoxylationofquinoxalin21honeswithfluoroalkylalcohols
AT sunjian visiblelightinducedaerobicc3hfluoroalkoxylationofquinoxalin21honeswithfluoroalkylalcohols
AT haoliqiang visiblelightinducedaerobicc3hfluoroalkoxylationofquinoxalin21honeswithfluoroalkylalcohols