N-Heterocyclic Carbene and Manganese Synergistic Catalysis: A Three-Component Radical Acylmonofluoroalkylation of Alkenes

被引:6
|
作者
Liang, Feng [1 ]
Chen, Ning [1 ]
Cheng, Keguang [1 ]
Wang, Quande [1 ]
机构
[1] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, Guilin 541004, Guangxi, Peoples R China
关键词
STYRENES; FLUORINE;
D O I
10.1021/acs.orglett.3c03461
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Despite the importance of monofluoroalkyl groups in pharmaceutically relevant molecules, catalytic protocols for their incorporation into alkenes remain limited. We describe herein a three-component acylmonofluoroalkylation of alkenes for the introduction of such moieties through an unprecedented cooperativity between the N-heterocyclic carbene catalyst and earth-abundant Mn-(II) complex. This general method can be applied to a variety of alkenes, including styrenes, 1,3-enynes, and allenes, as well as complex substrates containing natural product and drug motifs.
引用
收藏
页码:8168 / 8172
页数:5
相关论文
共 50 条
  • [41] N-Heterocyclic Carbene Catalysis under Oxidizing Conditions
    Dzieszkowski, Krzysztof
    Rafinski, Zbigniew
    CATALYSTS, 2018, 8 (11)
  • [42] N-Heterocyclic Carbene (NHC)/Metal Cooperative Catalysis
    Nagao, Kazunori
    Ohmiya, Hirohisa
    TOPICS IN CURRENT CHEMISTRY, 2019, 377 (06)
  • [43] β-Sulfonylation of α-bromoenals enabled by N-heterocyclic carbene catalysis
    Jin, Shiyi
    Fang, Shuaishuai
    Ma, Rui
    Liang, Zheng
    Xu, Ye
    Lu, Tao
    Du, Ding
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (19): : 3392 - 3396
  • [44] Discovering New Reactions with N-Heterocyclic Carbene Catalysis
    Phillips, Eric M.
    Chan, Audrey
    Scheidt, Karl A.
    ALDRICHIMICA ACTA, 2009, 42 (03) : 55 - 66
  • [45] Cooperative Lewis acid/N-heterocyclic carbene catalysis
    Cohen, Daniel T.
    Scheidt, Karl A.
    CHEMICAL SCIENCE, 2012, 3 (01) : 53 - 57
  • [46] N-Heterocyclic Carbene/Transition Metal Dual Catalysis
    Zhang, Zhao-Fei
    Zhang, Chun-Lin
    Ye, Song
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (54)
  • [47] N-heterocyclic carbene catalysts for hydrogenation of dienes and alkenes.
    Burgess, K
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U786 - U786
  • [48] Insights into the Three-Component Coupling Reactions of Aldehydes, Alkynes, and Amines Catalyzed by N-heterocyclic Carbene Silver: A DFT Study
    Zhang, Chenggen
    Yu, Shuyuan
    Wang, Fei
    Cao, Jian
    Liang, Xinru
    Wang, Fuping
    Zheng, Huimin
    Zhang, Yaning
    Yang, Mengyao
    Zhao, Boyu
    CATALYSTS, 2023, 13 (04)
  • [49] N-heterocyclic carbene (NHC)-modulated Pd/Cu cocatalyzed three-component synthesis of 2,6-diarylquinolines
    Xu, Chen
    Li, Hong-Mei
    Yuan, Xiao-Er
    Xiao, Zhi-Qiang
    Wang, Zhi-Qiang
    Fu, Wei-Jun
    Ji, Bao-Ming
    Hao, Xin-Qi
    Song, Mao-Ping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (19) : 3114 - 3122
  • [50] N-heterocyclic carbene-catalyzed radical reactions
    Kun-Quan Chen
    He Sheng
    Qiang Liu
    Pan-Lin Shao
    Xiang-Yu Chen
    Science China(Chemistry), 2021, 64 (01) : 7 - 16