Radical Fluoroalkylation Reactions

被引:213
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
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 [J].
Bao, Xifei ;
Liu, Lihua ;
Li, Junlan ;
Fan, Shilu .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) :463-468
[3]   Late stage trifluoromethylthiolation strategies for organic compounds [J].
Barata-Vallejo, Sebastian ;
Bonesi, Sergio ;
Postigo, Al .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (30) :7150-7182
[4]   Benign Perfluoroalkylation of Aniline Derivatives through Photoredox Organocatalysis under Visible-Light Irradiation [J].
Barata-Vallejo, Sebastian ;
Yerien, Damian E. ;
Postigo, Al .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (36) :7869-7875
[5]   Photocatalytic fluoroalkylation reactions of organic compounds [J].
Barata-Vallejo, Sebastian ;
Bonesi, Sergio M. ;
Postigo, Al .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) :11153-11183
[6]   Perfluoroalkylation reactions of (hetero)arenes [J].
Barata-Vallejo, Sebastian ;
Bonesi, Sergio M. ;
Postigo, Al .
RSC ADVANCES, 2015, 5 (77) :62498-62518
[7]   Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents [J].
Barata-Vallejo, Sebastian ;
Lantano, Beatriz ;
Postigo, Al .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) :16806-16829
[8]   Metal-mediated radical perfluoroalkylation of organic compounds [J].
Barata-Vallejo, Sebastian ;
Postigo, Al .
COORDINATION CHEMISTRY REVIEWS, 2013, 257 (21-22) :3051-3069
[9]   Anthraquinones as Photoredox Catalysts for the Reductive Activation of Aryl Halides [J].
Bardagi, Javier I. ;
Ghosh, Indrajit ;
Schmalzbauer, Matthias ;
Ghosh, Tamal ;
Koenig, Burkhard .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (01) :34-40
[10]   Perfluoroalkylation of Alkenes by Frustrated Lewis Pairs [J].
Behrends, Ilona ;
Baehr, Susanne ;
Czekelius, Constantin .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (48) :17177-17181