Photoredox Defluorinative Alkylation of 1-Trifluoromethyl Alkenes and 1,3-Butadienes with 1,4-Dihydropyridines as Alkylation Reagents

被引:53
作者
Chen, Haoguo [1 ]
Anand, Devireddy [1 ]
Zhou, Lei [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem, 135 Xingang West Rd, Guangzhou 510275, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
alkylation; C-F bond cleavage; difluoroalkenes; photoredox; radicals; NUCLEOPHILIC 5-ENDO-TRIG CYCLIZATION; GEM-DIFLUOROALKENES; ADDITION-REACTION; RADICAL-ADDITION; ALPHA; FLUORINE; 4-ALKYL-1,4-DIHYDROPYRIDINES; FUNCTIONALIZATION; ELIMINATION; ESTERS;
D O I
10.1002/ajoc.201900026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A radical defluorinative alkylation method of 1-trifluoromethyl alkenes and 1,3-butadienes with 4-alkyl-1,4-dihydropyridines under visible light irradiation is presented. Various alkylated 1,1-difluoroalkenes and 1,1-difluorodienes were obtained in moderate to high yields through a sequential C-C and C-F bond cleavage process.
引用
收藏
页码:661 / 664
页数:4
相关论文
共 56 条
  • [1] C-F Bond Activation in Organic Synthesis
    Amii, Hideki
    Uneyama, Kenji
    [J]. CHEMICAL REVIEWS, 2009, 109 (05) : 2119 - 2183
  • [2] Barski OA, 2008, DRUG METAB REV, V40, P553, DOI [10.1080/03602530802431439, 10.1080/03602530802431439 ]
  • [3] The Use of Fluoride as a Leaving Group: SN2' Displacement of a C?F Bond on 3,3-Difluoropropenes with Organolithium Reagents To Give Direct Access to Monofluoroalkenes
    Bergeron, Maxime
    Johnson, Thomas
    Paquin, Jean-Francois
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) : 11112 - 11116
  • [4] ADDITION-REACTION OF 3,3,3-TRIFLUOROPROPENE TO TETRAHYDROFURAN - TELOMERIC GROWTH VIA FREE-RADICAL REARRANGEMENTS
    BERGSTROM, DE
    NG, MW
    WONG, JJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (04): : 741 - 745
  • [5] Buzzetti L., 2017, ANGEW CHEMIE, V129, P15235
  • [6] Radical-Based C-C Bond-Forming Processes Enabled by the Photoexcitation of 4-Alkyl-1,4-dihydropyridines
    Buzzetti, Luca
    Prieto, Alexis
    Roy, Sudipta Raha
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (47) : 15039 - 15043
  • [7] Chambers R.D., 1997, ORGANOFLUORINE CHEM
  • [8] Synthesis and Metal-Catalyzed Reactions of gem-Dihalovinyl Systems
    Chelucci, Giorgio
    [J]. CHEMICAL REVIEWS, 2012, 112 (03) : 1344 - 1462
  • [9] Synthesis of Fluorinated Benzo[a]quinolizidines via Visible Light-induced Tandem Substitution of Two Fluorine Atoms in a CF3 Group
    Chen, Haoguo
    Xiao, Tiebo
    Li, Linyong
    Anand, Devireddy
    He, Yuwei
    Zhou, Lei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (20) : 3642 - 3647
  • [10] Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis
    Chen, Wenxin
    Liu, Zheng
    Tian, Jiaqi
    Li, Jin
    Ma, Jing
    Cheng, Xu
    Li, Guigen
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (38) : 12312 - 12315