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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Bibliographic Details
Published inOrganic letters Vol. 22; no. 15; pp. 5984 - 5989
Main Authors He, Xiang-Kui, Lu, Juan, Zhang, Ai-Jun, Zhang, Qing-Qing, Xu, Guo-Yong, Xuan, Jun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2020
Amer Chemical Soc
Subjects
alkylation
Chemistry
Chemistry, Organic
irradiation
light
Physical Sciences
Science & Technology
C-H ALKYLATION
CATALYSIS
REAGENTS
PHOTOREDOX
ACIDS
CHEMISTRY
TRANSFER HYDROGENATION
4-ALKYL-1,4-DIHYDROPYRIDINES
HANTZSCH ESTERS
DECARBOXYLATIVE ALKYNYLATION
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Summary: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
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c02080