NHC-Catalyzed Radical Tandem Cyclization/Coupling Reaction for the Synthesis of 2-Pyrrolidinone Derivatives

被引:2
|
作者
Zhou, Nengneng [1 ]
Wang, Lei [1 ]
Zhao, Fangli [1 ]
Gao, Xiang [1 ]
Zhao, Xiaowei [1 ]
Zhang, Man [1 ,2 ]
机构
[1] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Functionalized Mol Solids, Anhui Key Lab Mol Based Mat,Minist Educ, Wuhu 241000, Anhui, Peoples R China
[2] Anhui Normal Univ, Sch Phys & Elect Informat, Wuhu 241000, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
metal-free; NHC-catalyzed; 2-pyrrolidinons; radical coupling; tandem radical cyclization; EFFICIENT SYNTHESIS; GAMMA-LACTAMS; CARBENE; AMINODIFLUOROALKYLATION; ALKENES;
D O I
10.1002/ajoc.202300334
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel strategy for synthesizing structurally diverse 2-pyrrolidinons by a NHC-catalyzed tandem radical cyclization process has been developed. This reaction proceeds through a radical coupling approach, which not only shows broad substrate scope with excellent functional group compatibility but also is quite compatible with the secondary and tertiary radicals. By using this protocol, various potentially bioactive 2-pyrrolidinons were facilely synthesized.
引用
收藏
页数:5
相关论文
共 50 条
  • [1] Synthesis of 2-pyrrolidinone derivatives via N-heterocyclic carbene catalyzed radical tandem cyclization/coupling reactions
    Yin, Huiping
    Huang, Tianjiao
    Shi, Bai
    Cao, Wei
    Yu, Chenxia
    Li, Tuanjie
    Zhang, Kai
    Yao, Changsheng
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (11) : 2695 - 2700
  • [2] NHC-Catalyzed Regioselective Intramolecular Radical Cyclization Reaction for the Synthesis of Benzazepine Derivatives
    Zhou, Nengneng
    Zhao, Fangli
    Wang, Lei
    Gao, Xiang
    Zhao, Xiaowei
    Zhang, Man
    [J]. ORGANIC LETTERS, 2023, 25 (32) : 6072 - 6076
  • [3] NHC-Catalyzed Tandem Reaction: A Strategy for the Synthesis of 2-Pyrrolidinone-Functionalized Phenanthridines
    Zhou, Nengneng
    Wang, Lei
    Zhao, Fangli
    Gao, Xiang
    Zhao, Xiaowei
    Zhang, Man
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (23): : 16556 - 16565
  • [4] NHC catalyzed radical tandem cyclization: an efficient synthesis of α,α-difluoro-γ-lactam derivatives
    Huang, Tianjiao
    Yin, Huiping
    Li, Tuanjie
    Yu, Chenxia
    Zhang, Kai
    Yao, Changsheng
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (34) : 6988 - 6998
  • [5] NHC-catalyzed oxidative cyclization reaction for the synthesis of 3-substituted phthalides
    Youn, So Won
    Song, Hyoung Sub
    Park, Jong Hyub
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (15) : 2388 - 2393
  • [6] Highly Enantioselective Synthesis of α-Amino Acid Derivatives by an NHC-Catalyzed Intermolecular Stetter Reaction
    Jousseaume, Thierry
    Wurz, Nathalie E.
    Glorius, Frank
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) : 1410 - 1414
  • [7] Highly enantioselective synthesis of α-amino acid derivatives by an NHC-catalyzed intermolecular Stetter reaction
    Wurz, Nathalie E.
    Jousseaume, Thierry
    Schedler, Michael
    Glorius, Frank
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [8] Diastereoselective congested [3-amido ketone synthesis via NHC-catalyzed radical-radical coupling
    Sato, Yukiya
    Miyamoto, Yusuke
    Matsui, Takanori
    Sumida, Yuto
    Ohmiya, Hirohisa
    [J]. CHEM CATALYSIS, 2023, 3 (09):
  • [9] γ-Difluoroalkylation: Synthesis of γ-Difluoroalkyl-α,β-Unsaturated Esters via Photoredox NHC-Catalyzed Radical Reaction
    Dai, Lei
    Xu, Yuan-Yuan
    Xia, Zi-Hao
    Ye, Song
    [J]. ORGANIC LETTERS, 2020, 22 (20) : 8173 - 8177
  • [10] NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives
    Ji, Hong
    Zou, Juan
    Mou, Chengli
    Liu, Yonggui
    Ren, Shi-Chao
    Chi, Yonggui Robin
    [J]. CHEMICAL COMMUNICATIONS, 2023, 59 (42) : 6351 - 6354