Literature DB >> 30372088

Metal-Free C(sp2)-H/N-H Cross-Dehydrogenative Coupling of Quinoxalinones with Aliphatic Amines under Visible-Light Photoredox Catalysis.

Wei Wei1,2,3, Leilei Wang1, Pengli Bao1, Yun Shao2, Huilan Yue2, Daoshan Yang1,3, Xiaobo Yang4, Xiaohui Zhao2, Hua Wang1.   

Abstract

A novel and efficient visible-light-induced C(sp2)-H/N-H cross-dehydrogenative coupling (CDC)-amination with both primary and secondary aliphatic amines at room temperature in air is developed. This photocatalytic reaction allows the direct formation of 3-aminoquinoxalin-2(1 H)-ones via CDC-amination in the absence of any external oxidant added from outside. Preliminary mechanistic studies reveal that the present reaction proceeds through a radical process.

Entities:  

Year:  2018        PMID： 30372088     DOI： 10.1021/acs.orglett.8b03079

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 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

Review 2.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

Review 3.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

4.  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

5.  Sustainable Synthetic Approach for (Pyrazol-4-ylidene)pyridines By Metal Catalyst-Free Aerobic C(sp2)-C(sp3) Coupling Reactions between 1-Amino-2-imino-pyridines and 1-Aryl-5-pyrazolones.

Authors:  Hamada Mohamed Ibrahim; Haider Behbehani
Journal:  ACS Omega       Date:  2019-07-05

6.  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

7.  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

8.  Sunlight Induced and Recyclable g-C3N4 Catalyzed C-H Sulfenylation of Quinoxalin-2(1H)-Ones.

Authors:  Sha Peng; Jiao Liu; Li-Hua Yang; Long-Yong Xie
Journal:  Molecules       Date:  2022-08-08       Impact factor: 4.927
  8 in total

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