Visible Light-Induced Umpolung Synthesis of 3,3-Disubstituted Oxindoles via the Substrate-Photosensitive Strategy  

作　　者：Jingjing Yang Tingting Wang Benhui Sui Hongyu Wang Bo Tang 

机构地区：[1]Key Laboratory of Marine Drugs,Ministry of Education/Molecular Synthesis Center,and School Of Medicine and Pharmacy,Ocean Universityof China,Qingdao,Shandong 266003,China [2]Laboratory for Marine Drugs and Bioproducts,Qingdao Marine Science and Technology Center,Qingdao,Shandong 266237,China [3]College of Chemistry,Chemical Engineering and Materials Science,Shandong Normal University,Jinan,Shandong 250014,China [4]Laoshan Laboratory,Qingdao,Shandong 266237,China [5]Shandong Tai'an Ecological Environment Monitoring Center,Tai'an,Shandong 271000,China

出　　处：《Chinese Journal of Chemistry》2025年第4期431-436,共6页中国化学(英文版)

基　　金：support from the National Natural Science Foundation of China(22377113,21927811,22134004);the Taishan Scholar Program of Shandong Province(tsqn202306103);the Fundamental Research Funds for the Central Universities(Ocean University of China)is greatly appreciated.

摘　　要：3,3-Disubstituted oxindoles,forming the core of extensive bioactive natural products and drugs,attract tremendous efforts to develop efficient methods for their preparation.Here,a photocatalyst-free approach for the synthesis of 3,3-disubstituted oxindoles via a substrate-photosensitive strategy under visible light was successfully developed.Preliminary mechanistic studies illustrated that isatin-derived imines can be directly excited by visible light to generate strong oxidant states,facilitating subsequent single-electron transfer(SET)processes with Hantzsch esters to afford the correspondingα-amino radical intermediates.Thus,theseα-amino radicals promote the subsequent Giese radical addition or radical/radical cross-coupling reactions to furnish diverse functionalized 3-substituted 3-aminooxindoles in high yields.

关 键 词：Umpolung synthesis Photocatalysis α-Amino radical Isatin-derived imines 3-Substituted 3-aminooxindoles 

分 类 号：O62[理学—有机化学]