BI-OAc-Accelerated C3–H Alkylation of Quinoxalin-2(1H)‑ones under Visible-Light Irradiation
An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexci...
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| Published in | Organic letters Vol. 22; no. 15; pp. 5984 - 5989 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
07.08.2020
Amer Chemical Soc |
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| Abstract | An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope of both quinoxalin-2(1H)-ones and R-DHPs. The synthetic value of the protocol was also demonstrated by the successful functionalization of natural products and drug-based complex molecules |
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| AbstractList | An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope of both quinoxalin-2(1H)-ones and R-DHPs. The synthetic value of the protocol was also demonstrated by the successful functionalization of natural products and drug-based complex molecules An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope of both quinoxalin-2(1H)-ones and R-DHPs. The synthetic value of the protocol was also demonstrated by the successful functionalization of natural products and drug-based complex molecules An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope of both quinoxalin-2(1H)-ones and R-DHPs. The synthetic value of the protocol was also demonstrated by the successful functionalization of natural products and drug-based complex molecules.An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope of both quinoxalin-2(1H)-ones and R-DHPs. The synthetic value of the protocol was also demonstrated by the successful functionalization of natural products and drug-based complex molecules. An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1 )-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope of both quinoxalin-2(1 )-ones and R-DHPs. The synthetic value of the protocol was also demonstrated by the successful functionalization of natural products and drug-based complex molecules. |
| Author | Lu, Juan Xuan, Jun Xu, Guo-Yong Zhang, Ai-Jun He, Xiang-Kui Zhang, Qing-Qing |
| AuthorAffiliation | (Anhui University), Ministry of Education Institute of Physical Science and Information Technology Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry & Chemical Engineering Key Laboratory of Structure and Functional Regulation of Hybrid Materials |
| AuthorAffiliation_xml | – name: (Anhui University), Ministry of Education – name: Institute of Physical Science and Information Technology – name: Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry & Chemical Engineering – name: Key Laboratory of Structure and Functional Regulation of Hybrid Materials |
| Author_xml | – sequence: 1 givenname: Xiang-Kui surname: He fullname: He, Xiang-Kui organization: Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry & Chemical Engineering – sequence: 2 givenname: Juan surname: Lu fullname: Lu, Juan organization: Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry & Chemical Engineering – sequence: 3 givenname: Ai-Jun surname: Zhang fullname: Zhang, Ai-Jun organization: Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry & Chemical Engineering – sequence: 4 givenname: Qing-Qing surname: Zhang fullname: Zhang, Qing-Qing organization: Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry & Chemical Engineering – sequence: 5 givenname: Guo-Yong surname: Xu fullname: Xu, Guo-Yong organization: Institute of Physical Science and Information Technology – sequence: 6 givenname: Jun orcidid: 0000-0003-0578-9330 surname: Xuan fullname: Xuan, Jun email: xuanjun@ahu.edu.cn organization: (Anhui University), Ministry of Education |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32705873$$D View this record in MEDLINE/PubMed |
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| Keywords | C-H ALKYLATION CATALYSIS REAGENTS PHOTOREDOX ACIDS CHEMISTRY TRANSFER HYDROGENATION 4-ALKYL-1,4-DIHYDROPYRIDINES HANTZSCH ESTERS DECARBOXYLATIVE ALKYNYLATION |
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| Snippet | An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines... An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines... An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1 )-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines... |
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| SubjectTerms | alkylation Chemistry Chemistry, Organic irradiation light Physical Sciences Science & Technology |
| Title | BI-OAc-Accelerated C3–H Alkylation of Quinoxalin-2(1H)‑ones under Visible-Light Irradiation |
| URI | http://dx.doi.org/10.1021/acs.orglett.0c02080 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000562077400053 https://www.ncbi.nlm.nih.gov/pubmed/32705873 https://www.proquest.com/docview/2427304114 https://www.proquest.com/docview/2551908981 |
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