Benzylic C(sp 3 )-H fluorination

被引：2

作者：

Atkins, Alexander P. ^{[1
]}

Dean, Alice C. ^{[1
]}

Lennox, Alastair J. J. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, England

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 20卷

基金：

欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

benzylic; C-H functionalization; fluorination; photoredox catalysis; C-H FLUORINATION; CHEMISTRY RESEARCH AREAS; ELECTROLYTIC FLUORINATIONS; ANODIC FLUORINATION; C(SP(3))-H BONDS; AMINO-ACIDS; LIGHT; FUNCTIONALIZATION; DIFLUORINATION; PERSPECTIVE;

D O I：

10.3762/bjoc.20.137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selective fluorination of C(sp 3 )-H bonds is an attractive target, particularly for pharmaceutical and agrochemical applications. Consequently, over recent years much attention has been focused on C(sp 3 )-H fluorination, and several methods that are selective for benzylic C-H bonds have been reported. These protocols operate via several distinct mechanistic pathways and involve a variety of fluorine sources with distinct reactivity profiles. This review aims to give context to these transformations and strategies, highlighting the different tactics to achieve fluorination of benzylic C-H bonds.

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页码：1527 / 1547

页数：21

相关论文

共 104 条

[1] Achievements in fluorination using variable reagents through a deoxyfluorination reaction [J].

Aggarwal, Trapti ;

Sushmita ;

Verma, Akhilesh K. .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (22) :6452-6468

[2] 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

[3] Pulsed electrolysis: enhancing primary benzylic C(sp3)-H nucleophilic fluorination [J].

Atkins, Alexander P. ;

Chaturvedi, Atul K. ;

Tate, Joseph A. ;

Lennox, Alastair J. J. .

ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (03) :802-808

[4] Fluorous Synthesis of 18F Radiotracers with the [18F]Fluoride Ion: Nucleophilic Fluorination as the Detagging Process [J].

Bejot, Romain ;

Fowler, Thomas ;

Carroll, Laurence ;

Boldon, Sophie ;

Moore, Jane E. ;

Declerck, Jerome ;

Gouverneur, Veronique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :586-589

[5] Photocatalyzed Benzylic Fluorination: Shedding "Light" on the Involvement of Electron Transfer [J].

Bloom, Steven ;

McCann, Michael ;

Lectka, Thomas .

ORGANIC LETTERS, 2014, 16 (24) :6338-6341

[6] 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

[7] 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

[8] Key Green Chemistry research areas from a pharmaceutical manufacturers' perspective revisited [J].

Bryan, Marian C. ;

Dunn, Peter J. ;

Entwistle, David ;

Gallou, Fabrice ;

Koenig, Stefan G. ;

Hayler, John D. ;

Hickey, Matthew R. ;

Hughes, Shaun ;

Kopach, Michael E. ;

Moine, Gerard ;

Richardson, Paul ;

Roschangar, Frank ;

Steven, Alan ;

Weiberth, Franz J. .

GREEN CHEMISTRY, 2018, 20 (22) :5082-5103

[9] Recent Advances in Visible Light-mediated Fluorination [J].

Bui, Tien Tan ;

Hong, Wan Pyo ;

Kim, Hee-Kwon .

JOURNAL OF FLUORINE CHEMISTRY, 2021, 247

[10] Catalyzed and Promoted Aliphatic Fluorination [J].

Bume, Desta Doro ;

Harry, Stefan Andrew ;

Lectka, Thomas ;

Pitts, Cody Ross .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16) :8803-8814

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