Axially Chiral C2-Symmetric N-Heterocyclic Carbene (NHC) Palladium Complex-Catalyzed Asymmetric Fluorination and Amination of Oxindoles

被引:32
|
作者
Zhang Rui [1 ,2 ]
Wang De [1 ,2 ]
Xu Qin [1 ,2 ]
Jiang Jiajun [1 ,2 ]
Shi Min [1 ,2 ,3 ]
机构
[1] E China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
chiral C2-symmetric N-heterocyclic carbene (NHC) palladium diaquo complex; (S)-BINAM; asymmetric fluorination of oxindoles; N-fluorobenzenesulfonimide (NFSI); 1-chloromethyl-4-fluoro-1; 4-diazoniabicyclo[2; 2; 2]octane bis(tetrafluoroborate) (selectfluor); ORGANOCATALYTIC ALPHA-FLUORINATION; BETA-KETO PHOSPHONATES; ENANTIOSELECTIVE FLUORINATION; ARYLBORONIC ACIDS; ELECTROPHILIC FLUORINATION; MEDICINAL CHEMISTRY; ATOM-TRANSFER; IONIC LIQUID; CHLORINATION; COMBINATIONS;
D O I
10.1002/cjoc.201200289
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral C2-symmetric N-heterocyclic carbene (NHC) palladium diaquo complex 5b prepared from (S)-BINAM was found to be a fairly effective catalyst for the enantioselective asymmetric fluorination of oxindoles to give the corresponding products in moderate enantioselectivities along with good to excellent yields.
引用
收藏
页码:1295 / 1304
页数:10
相关论文
共 50 条
  • [41] Stereospecific Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Redox Synthesis of Trifluoromethyl Dihydropyranones and Mechanistic Insights
    Davies, Alyn T.
    Taylor, James E.
    Douglas, James
    Collett, Christopher J.
    Morrill, Louis C.
    Fallan, Charlene
    Slawin, Alexandra M. Z.
    Churchill, Gwydion
    Smith, Andrew D.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18): : 9243 - 9257
  • [42] An Iridium(I) N-Heterocyclic Carbene Complex Catalyzes Asymmetric Intramolecular Allylic Amination Reactions
    Ye, Ke-Yin
    Cheng, Qiang
    Zhuo, Chun-Xiang
    Dai, Li-Xin
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (28) : 8113 - 8116
  • [43] SYNTHESIS OF A NEW CHIRAL C2-SYMMETRIC NHC-AuCl COMPLEX
    Okitsu, Naoya
    Yoshida, Takuya
    Usui, Kensuke
    Nakada, Masahisa
    HETEROCYCLES, 2016, 92 (04) : 720 - 732
  • [44] N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed Amination between Aryl Chlorides and Amides
    Chen, Wen-Xin
    Shao, Li-Xiong
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9236 - 9239
  • [45] Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkyl Amides
    Wang, Chang-An
    Rahman, Md Mahbubur
    Bisz, Elwira
    Szostak, Roman
    Dziuk, Blazej
    Szostak, Michal
    ACS CATALYSIS, 2022, 12 (04) : 2426 - 2433
  • [46] N-heterocyclic carbene-palladium complex catalyzed oxidative carbonylation of amines to ureas
    Zheng Shu-Zhan
    Peng Xin-Gao
    Liu Jian-Ming
    Sun Wei
    Xia Chun-Gu
    CHINESE JOURNAL OF CHEMISTRY, 2007, 25 (08) : 1065 - 1068
  • [47] N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of Axially Chiral α-Carbolinones via Heterocycle Formation
    Wang, Hai-Ying
    Li, Zhi-Cheng
    Zhang, Chun-Lin
    Ye, Song
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16): : 11913 - 11923
  • [48] SYNTHESIS OF ENANTIOENRICHED INDOLOPIPERAZINONES VIA IRIDIUM(I) N-HETEROCYCLIC CARBENE COMPLEX CATALYZED ASYMMETRIC INTRAMOLECULAR ALLYLIC AMINATION REACTION
    Ye, Ke-Yin
    Wu, Ke-Jia
    Li, Guo-Tai
    Dai, Li-Xin
    You, Shu-Li
    HETEROCYCLES, 2017, 95 (01) : 304 - 313
  • [49] Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI
    Organ, Michael G.
    Abdel-Hadi, Mirvat
    Avola, Stephanie
    Dubovyk, Igor
    Hadei, Niloufar
    Kantchev, Eric Assen B.
    O'Brien, Christopher J.
    Sayah, Mahmoud
    Valente, Cory
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (08) : 2443 - 2452
  • [50] N-heterocyclic carbene-Pd(II)-2-methyl-4,5-dihydrooxazole complex-catalyzed highly chemoselective mono-amination of dichlorobenzenes
    Sun, Kai-Xin
    Zhou, Jin-Hui
    He, Qian-Wei
    Shao, Li-Xiong
    Lu, Jian-Mei
    TETRAHEDRON, 2020, 76 (08)