Late-Stage Fluorination: From Fundamentals to Application

被引:163
作者
Campbell, Michael G. [1 ]
Ritter, Tobias [1 ]
机构
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
基金
美国国家科学基金会;
关键词
COPPER-MEDIATED FLUORINATION; BETA-FLUORIDE ELIMINATION; BOND FORMATION; TRIFLUOROMETHYL TRIFLATE; REDUCTIVE ELIMINATION; ARYL STANNANES; F BOND; PALLADIUM; CHEMISTRY; MECHANISM;
D O I
10.1021/op400349g
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this brief account, we review work from our lab with a focus on late-stage introduction of fluorine and fluorinated functional groups into small molecules. We attempt to highlight practical developments, which we believe may have potential for industrial applications, and critically reflect on developments that may not yet meet the bar for practical use.
引用
收藏
页码:474 / 480
页数:7
相关论文
共 51 条
[1]   Molecular imaging with PET [J].
Ametamey, Simon M. ;
Honer, Michael ;
Schubiger, Pius August .
CHEMICAL REVIEWS, 2008, 108 (05) :1501-1516
[2]  
[Anonymous], 2011, Angew. Chem., DOI [10.1002/ange.201102543, DOI 10.1002/ANGE.201102543]
[3]   Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex [J].
Ball, Nicholas D. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :3796-+
[4]   Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent [J].
Boursalian, Gregory B. ;
Ngai, Ming-Yu ;
Hojczyk, Katarzyna N. ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (36) :13278-13281
[5]  
Brandt JR, 2014, CHEM SCI, V5, P169, DOI [10.1039/C3SC52367E, 10.1039/c3sc52367e]
[6]   Carrier-effect on palladium-catalyzed, nucleophilic 18F-fluorination of aryl triflates [J].
Cardinale, Jens ;
Ermert, Johannes ;
Kuegler, Fabian ;
Helfer, Andreas ;
Brandt, Marie R. ;
Coenen, Heinz H. .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2012, 55 (12) :450-453
[7]   Crystal structure and mechanism of a bacterial fluorinating enzyme [J].
Dong, CJ ;
Huang, FL ;
Deng, H ;
Schaffrath, C ;
Spencer, JB ;
O'Hagan, D ;
Naismith, JH .
NATURE, 2004, 427 (6974) :561-565
[8]  
Emsley J, 1980, CHEM SOC REV, V9, P19
[9]   Copper-Mediated Fluorination of Arylboronate Esters. Identification of a Copper(III) Fluoride Complex [J].
Fier, Patrick S. ;
Luo, Jingwei ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (07) :2552-2559
[10]   Copper-Mediated Fluorination of Aryl Iodides [J].
Fier, Patrick S. ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) :10795-10798