Radical Fluoroalkylation Reactions

被引:200
作者
Barata-Vallejo, Sebastian [1 ]
Victoria Cooke, Maria [1 ]
Postigo, Al [1 ]
机构
[1] Univ Buenos Aires, Fac Farm & Bioquim, Dept Quim Organ, Junin 954, RA-1113 Buenos Aires, DF, Argentina
来源
ACS CATALYSIS | 2018年 / 8卷 / 08期
关键词
perfluoroalkylation; organophotocatalysis; transition metal photocatalysis; EDA complex; FLP perfluoroalkylation; catalytic perfluoroalkylations; LIGHT-INDUCED TRIFLUOROMETHYLATION; DONOR-ACCEPTOR COMPLEX; FRUSTRATED LEWIS PAIRS; ENANTIOSELECTIVE PERFLUOROALKYLATION; CATALYZED PERFLUOROALKYLATION; ASYMMETRIC FLUORINATION; ISOCYANIDE INSERTION; PHOTOREDOX CATALYSIS; TERMINAL ALKENES; FACILE ACCESS;
D O I
10.1021/acscatal.8b02066
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Recent protocols and reactions for catalytic radical perfluoroalkylations will be described. The production of perfluoroalkyl radicals (R-F = CnF2n+1, n >= 2), which effect both addition and substitution reactions on organic substrates, can be realized through a range of diverse methods such as the well-established visible-light transition-metal-mediated photocatalysis, organic-dye-photocatalyzed reactions, electron donoracceptor complexes, and more recently frustrated Lewis pairs. Thus, perfluoroalkylation reactions of carboncarbon multiple bonds, isocyanides, nitrones, hydrazones, beta-keto esters, a-cyano arylacetates, sulfides, and (hetero)arenes will be described. Special emphasis will be placed on examples published after 2015, where higher fluorinated series of fluoroalkylating reagents are studied.
引用
收藏
页码:7287 / 7307
页数:41
相关论文
共 127 条
  • [1] Arceo E, 2013, NAT CHEM, V5, P750, DOI [10.1038/NCHEM.1727, 10.1038/nchem.1727]
  • [2] Copper-Catalyzed Oxidative Perfluoroalkylation of Aryl Boronic Acids Using Perfluoroalkylzinc Reagents
    Bao, Xifei
    Liu, Lihua
    Li, Junlan
    Fan, Shilu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) : 463 - 468
  • [3] Late stage trifluoromethylthiolation strategies for organic compounds
    Barata-Vallejo, Sebastian
    Bonesi, Sergio
    Postigo, Al
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (30) : 7150 - 7182
  • [4] Benign Perfluoroalkylation of Aniline Derivatives through Photoredox Organocatalysis under Visible-Light Irradiation
    Barata-Vallejo, Sebastian
    Yerien, Damian E.
    Postigo, Al
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (36) : 7869 - 7875
  • [5] Photocatalytic fluoroalkylation reactions of organic compounds
    Barata-Vallejo, Sebastian
    Bonesi, Sergio M.
    Postigo, Al
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11153 - 11183
  • [6] Perfluoroalkylation reactions of (hetero)arenes
    Barata-Vallejo, Sebastian
    Bonesi, Sergio M.
    Postigo, Al
    [J]. RSC ADVANCES, 2015, 5 (77) : 62498 - 62518
  • [7] Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents
    Barata-Vallejo, Sebastian
    Lantano, Beatriz
    Postigo, Al
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) : 16806 - 16829
  • [8] Metal-mediated radical perfluoroalkylation of organic compounds
    Barata-Vallejo, Sebastian
    Postigo, Al
    [J]. COORDINATION CHEMISTRY REVIEWS, 2013, 257 (21-22) : 3051 - 3069
  • [9] Anthraquinones as Photoredox Catalysts for the Reductive Activation of Aryl Halides
    Bardagi, Javier I.
    Ghosh, Indrajit
    Schmalzbauer, Matthias
    Ghosh, Tamal
    Koenig, Burkhard
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (01) : 34 - 40
  • [10] Perfluoroalkylation of Alkenes by Frustrated Lewis Pairs
    Behrends, Ilona
    Baehr, Susanne
    Czekelius, Constantin
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (48) : 17177 - 17181