Synthesis of difluoromethylated 2-oxindoles and quinoline-2,4-diones via visible light-induced tandem radical cyclization of N-arylacrylamides
Visible light-induced difluoromethylation of N-arylacrylamides to afford difluoromethylated 2-oxindoles and quinoline-2,4-diones with difluoromethyl 2-pyridyl sulfones as radical precursors has been disclosed. This method provides convenient access to a variety of 2-oxindoles and quinoline-2,4-diones under mild conditions via a proposed tandem radical addition/cyclization process along with good tolerance to various functional groups. In addition, preliminary experimental studies have revealed that water is a key factor in difluoromethylation and the reaction involves an oxidative quenching cycle of the photocatalyst.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2019 |
|---|---|
| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:17 |
|---|---|
| Enthalten in: |
Organic & biomolecular chemistry - 17(2019), 27 vom: 21. Juli, Seite 6629-6638 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Sun, Huan [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
|---|
| Anmerkungen: |
Date Completed 06.12.2019 Date Revised 17.12.2019 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1039/c9ob01213c |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM298602083 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM298602083 | ||
| 003 | DE-627 | ||
| 005 | 20231225094521.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231225s2019 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1039/c9ob01213c |2 doi | |
| 028 | 5 | 2 | |a pubmed24n0995.xml |
| 035 | |a (DE-627)NLM298602083 | ||
| 035 | |a (NLM)31246223 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Sun, Huan |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis of difluoromethylated 2-oxindoles and quinoline-2,4-diones via visible light-induced tandem radical cyclization of N-arylacrylamides |
| 264 | 1 | |c 2019 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 06.12.2019 | ||
| 500 | |a Date Revised 17.12.2019 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Visible light-induced difluoromethylation of N-arylacrylamides to afford difluoromethylated 2-oxindoles and quinoline-2,4-diones with difluoromethyl 2-pyridyl sulfones as radical precursors has been disclosed. This method provides convenient access to a variety of 2-oxindoles and quinoline-2,4-diones under mild conditions via a proposed tandem radical addition/cyclization process along with good tolerance to various functional groups. In addition, preliminary experimental studies have revealed that water is a key factor in difluoromethylation and the reaction involves an oxidative quenching cycle of the photocatalyst | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 700 | 1 | |a Jiang, Yue |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Ying-Sha |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Yun-Yun |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Lin |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Wen-Xuan |e verfasserin |4 aut | |
| 700 | 1 | |a Feng, Tao |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Zheng-Hui |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Ji-Kai |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Organic & biomolecular chemistry |d 2003 |g 17(2019), 27 vom: 21. Juli, Seite 6629-6638 |w (DE-627)NLM126779694 |x 1477-0539 |7 nnns |
| 773 | 1 | 8 | |g volume:17 |g year:2019 |g number:27 |g day:21 |g month:07 |g pages:6629-6638 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1039/c9ob01213c |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 17 |j 2019 |e 27 |b 21 |c 07 |h 6629-6638 | ||