Transition-metal-catalyzed C(sp3)-H 3 )-H bond fluorination reactions

被引:0
作者
Ge, Robbie [2 ]
Xu, Ziting [1 ]
Yang, Ke [1 ]
Ge, Haibo [2 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Jiangsu, Peoples R China
[2] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
来源
CHEM CATALYSIS | 2024年 / 4卷 / 07期
关键词
C-H FLUORINATION; TRANSIENT DIRECTING GROUPS; AMINO-ACIDS; LATE-STAGE; FUNCTIONALIZATION; ARYLATION; ACTIVATION; AUXILIARY; KETONES;
D O I
10.1016/j.checat.2024.101009
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
Constructing C- F bonds via C- H activation has been a subject of considerable attention in the field of organic synthesis. Within this reaction class, the popularity of transition-metal-catalyzed approaches has substantially expanded in recent years. Currently, there are two main types of these reaction pathways. The first type involves the formation of a carbon-metal-fluorine intermediate with the assistance of a directing group. The second type utilizes a transition metal species to generate a radical or carbocation intermediate. Despite the importance of these reactions, there has yet to be a comprehensive review of transition-metal-catalyzed C(sp3)-H 3 )- H bond fluorination processes. This review presents major advances in and detailed mechanistic discussions of transition-metal-catalyzed C(sp3)-H 3 )- H bond fluorination reactions with different reaction modes under various thermal, photochemical, and electrochemical conditions.
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页数:34
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共 124 条
[1]   Sustainable protocols for direct C-H bond arylation of (hetero)arenes [J].
Albano, Gianluigi ;
Punzi, Angela ;
Capozzi, Maria Annunziata M. ;
Farinola, Gianluca M. .
GREEN CHEMISTRY, 2022, 24 (05) :1809-1894
[2]   Progress and prospects in copper-catalyzed C-H functionalization [J].
Aneeja, Thaipparambil ;
Neetha, Mohan ;
Afsina, C. M. A. ;
Anilkumar, Gopinathan .
RSC ADVANCES, 2020, 10 (57) :34429-34458
[3]   Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom [J].
Babudri, Francesco ;
Farinola, Gianluca M. ;
Naso, Francesco ;
Ragni, Roberta .
CHEMICAL COMMUNICATIONS, 2007, (10) :1003-1022
[4]   Combining transition metals and transient directing groups for C-H functionalizations [J].
Bhattacharya, Trisha ;
Pimparkar, Sandeep ;
Maiti, Debabrata .
RSC ADVANCES, 2018, 8 (35) :19456-19464
[5]   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
[6]   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
[7]   C(sp3)-H Fluorination with a Copper(II)/(III) Redox Couple [J].
Bower, Jamey K. ;
Cypcar, Andrew D. ;
Henriquez, Brenda ;
Stieber, S. Chantal E. ;
Zhang, Shiyu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (18) :8514-8521
[8]   Palladium-Catalyzed Allylic C-H Fluorination [J].
Braun, Marie-Gabrielle ;
Doyle, Abigail G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) :12990-12993
[9]   Late-stage [18F]fluorination: new solutions to old problems [J].
Brooks, Allen F. ;
Topczewski, Joseph J. ;
Ichiishi, Naoko ;
Sanford, Melanie S. ;
Scott, Peter J. H. .
CHEMICAL SCIENCE, 2014, 5 (12) :4545-4553
[10]   Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Bronsted Base [J].
Buss, Joshua A. ;
Vasilopoulos, Aristidis ;
Golden, Dung L. ;
Stahl, Shannon S. .
ORGANIC LETTERS, 2020, 22 (15) :5749-5752