Vanadium-catalyzed C(sp3)-H fluorination reactions

被引:72
作者
Xia, Ji-Bao [1 ]
Ma, Yuyong [1 ]
Chen, Chuo [1 ]
机构
[1] Univ Texas SW Med Ctr Dallas, Div Chem, Dept Biochem, Dallas, TX 75390 USA
关键词
C-H FLUORINATION; ELECTROPHILIC FLUORINATION; METAL-FREE; UNACTIVATED ALKENES; OXIDATION; COMPLEXES; ALKANES; COPPER; HYDROXYLATION; AMINOFLUORINATION;
D O I
10.1039/c4qo00057a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Vanadium(III) oxide catalyzes the direct fluorination of C(sp(3))-H groups with Selectfluor. This reaction is operationally simple. The catalyst and the reaction by-product can be removed easily by filtration. Using this method, a fluorine atom can be introduced to the tertiary position of 1,4-cineole and L-menthone selectively.
引用
收藏
页码:468 / 472
页数:5
相关论文
共 72 条
[1]   Metal-Free Fluorination of C(sp3)-H Bonds Using a Catalytic N-Oxyl Radical [J].
Amaoka, Yuuki ;
Nagatomo, Masanori ;
Inoue, Masayuki .
ORGANIC LETTERS, 2013, 15 (09) :2160-2163
[2]   Fe(III)/NaBH4-Mediated Free Radical Hydrofluorination of Unactivated Alkenes [J].
Barker, Timothy J. ;
Boger, Dale L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13588-13591
[3]   A photocatalyzed aliphatic fluorination [J].
Bloom, Steven ;
Knippel, James Levi ;
Lectka, Thomas .
CHEMICAL SCIENCE, 2014, 5 (03) :1175-1178
[4]   Iron(II)-Catalyzed Benzylic Fluorination [J].
Bloom, Steven ;
Pitts, Cody Ross ;
Woltornist, Ryan ;
Griswold, Andrew ;
Holl, Maxwell Gargiulo ;
Lectka, Thomas .
ORGANIC LETTERS, 2013, 15 (07) :1722-1724
[5]   A Polycomponent Metal-Catalyzed Aliphatic, Allylic, and Benzylic Fluorination [J].
Bloom, Steven ;
Pitts, Cody Ross ;
Miller, David Curtin ;
Haselton, Nathan ;
Holl, Maxwell Gargiulo ;
Urheim, Ellen ;
Lectka, Thomas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (42) :10580-10583
[6]   Fluorine in medicinal chemistry [J].
Böhm, HJ ;
Banner, D ;
Bendels, S ;
Kansy, M ;
Kuhn, B ;
Müller, K ;
Obst-Sander, U ;
Stahl, M .
CHEMBIOCHEM, 2004, 5 (05) :637-643
[7]   Reactions of Late Transition Metal Complexes with Molecular Oxygen [J].
Boisvert, Luc ;
Goldberg, Karen I. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :899-910
[8]   MECHANISM OF ARENE HYDROXYLATION BY VANADIUM PICOLINATO PEROXO COMPLEXES [J].
BONCHIO, M ;
CONTE, V ;
DIFURIA, F ;
MODENA, G ;
MORO, S .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6262-6267
[9]   Catalytic, Mild, and Selective Oxyfunctionalization of Linear Alkanes: Current Challenges [J].
Bordeaux, Melanie ;
Galarneau, Anne ;
Drone, Jullien .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) :10712-10723
[10]   Palladium-Catalyzed Allylic C-H Fluorination [J].
Braun, Marie-Gabrielle ;
Doyle, Abigail G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) :12990-12993