Literature DB >> 31432590

Construction of C(sp2 )-C(sp3 ) Bond between Quinoxalin-2(1H)-ones and N-Hydroxyphthalimide Esters via Photocatalytic Decarboxylative Coupling.

Zhiyang Yan1, Bin Sun1, Xun Zhang2, Xiaohui Zhuang2, Jin Yang2, Weike Su1,2, Can Jin2.   

Abstract

A novel visible-light-driven decarboxylative coupling of alkyl N-hydroxyphthalimide esters (NHP esters) with quinoxalin-2(1H)-ones has been developed. This C(sp2 )-C(sp3 ) bond-forming transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note, a series of 3-primary alkyl-substituted quinoxalin-2(1H)-ones that were difficult to synthesize by previous methods could be obtained in moderate to excellent yields. Additionally, the mild conditions, easy availability of substrates, wide functional group tolerance and operational simplicity make this protocol practical in the synthesis of 3-alkylated quinoxalin-2(1H)-ones.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C(sp2)−C(sp3); NHP esters; metal- and oxidant-free; photoredox catalysis; quinoxalin-2(1H)-ones

Year:  2019        PMID: 31432590     DOI: 10.1002/asia.201900904

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  4 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

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

Authors:  Xiaobo Xu; Chengcai Xia; Xiaojun Li; Jian Sun; Liqiang Hao
Journal:  RSC Adv       Date:  2020-01-09       Impact factor: 4.036

3.  Regioselective C-3-alkylation of quinoxalin-2(1H)-ones via C-N bond cleavage of amine derived Katritzky salts enabled by continuous-flow photoredox catalysis.

Authors:  Gandhari Kishor; Vankudoth Ramesh; Vadithya Ranga Rao; Srihari Pabbaraja; Praveen Reddy Adiyala
Journal:  RSC Adv       Date:  2022-04-29       Impact factor: 4.036

4.  Photoinitiated decarboxylative C3-difluoroarylmethylation of quinoxalin-2(1H)-ones with potassium 2,2-difluoro-2-arylacetates in water.

Authors:  Yanhui Gao; Lulu Zhao; Tianyi Xiang; Pinhua Li; Lei Wang
Journal:  RSC Adv       Date:  2020-03-12       Impact factor: 4.036

  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.