Browse > Article
http://dx.doi.org/10.22643/JRMP.2017.3.2.122

Transition metal-mediated/catalyzed fluorination methodology developed in the 2000s  

Bae, Dae Young (Department of Chemistry, Pohang University of Science and Technology)
Lee, Eunsung (Department of Chemistry, Pohang University of Science and Technology)
Publication Information
Journal of Radiopharmaceuticals and Molecular Probes / v.3, no.2, 2017 , pp. 122-128 More about this Journal
Abstract
In the 2000s, there has been a significant advance on carbon-fluorine (C-F) bond formation reactions via transition metal mediated or catalyzed methods. Of course, for the past 10 years, transition metal catalysis improves C-F bond formation in terms of practicality and even can be applied to C-18F bond formation reaction. In this mini-review, we summarize various transition metal mediated or catalyzed fluorination reactions, which were developed in the mid-2000s.
Keywords
Fluorination; Carbon-fluorine; Transition metals; Catalysis;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Sakakura T, Chaisupakitsin M, Hayashi T, Tanaka M. Efficient acid fluoride synthesis via carbonylation of organic halides. J Organomet Chem 1987;334:205-211.   DOI
2 Okano T, Harada N, Kiji J. Catalytic Acid Fluoride Synthesis via Carbonylation of Organic Bromides in the Presence Potassium Fluoride. Bull Chem Soc Jpn 1992;65:1741-1743.   DOI
3 Hatanaka Y, Fukushima S, Hiyama T. Carbonylative coupling reaction of organofluorosilanes with organic halides promoted by fluoride ion and palldium catalyst. Tetrahedron 1992;48:2113-2126.   DOI
4 Prichard WW. U.S. Patent 2696503, 1954.
5 Mador IL, Scheben JA. U.S. Patent 3452090, 1969.
6 Prichard WW. U.S. Patent 3632643, 1972.
7 Grushin VV. Palladium Fluoride Complexes: one more step toward metal-mediated C-F bond formation. Chemistry. 2002;8:1006-1014.   DOI
8 Komiya S, Akai Y, Tanaka K, Yamamoto T, Yamamoto A. Reductive elimination of aryl carboxylates from acyl(aryloxy)nickel(II) and -palladium(II) complexes. Organometallics 1985;4:1130-1136.   DOI
9 Grushin VV, Alper H. Indirect Formation of Carboxylic Acids via Anhydrides in the Palladium-Catalyzed Hydroxycarbonylation of Aromatic Halides. J Am Chem Soc 1995;117:4305-4315.   DOI
10 Grushin VV, Alper H. Transformations of Chloroarenes, Catalyzed by Transition-Metal Complexes. Chem Rev 1994;94:1047-1062.   DOI
11 Grushin VV, Alper H. Activation of Otherwise Unreactive C-Cl Bonds. Top Organomet Chem 1999;3:193-226.
12 Hintermann L, Togni A. Catalytic Enantioselective Fluorination of ${\beta}$-Ketoesters. Angew Chem Int Ed 2000;39:4359-4362.   DOI
13 Bobbio C, Gouverneur V. Catalytic asymmetric fluorinations. Org Biomol Chem 2006;4:2065-2075.   DOI
14 Ma J-A, Cahard D. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions. 2004;104:6119-6146.   DOI
15 Ibrahim H, Togni A. Enantioselective halogenation reactions. Chem Commun 2004;0:1147-1155.
16 Hamashima Y, Takano H, Hotta D, Sodeoka M. Immobilization and reuse of Pd complexes in ionic liquid: efficient catalytic asymmetric fluorination and Michael reactions with beta-ketoesters. Org Lett 2003;5:3225-3228.   DOI
17 Barthazy P, Togni A, Mezzetti A. Catalytic Fluorination by Halide Exchange with 16-Electron Ruthenium(II) Complexes. X-ray Structure of [$Tl({\mu}-F)_2Ru(dppe)_2$]$PF_6$. Organometallics 2001;20:3472-3477.   DOI
18 Bonaccorsi C, Mezzetti A. Ruthenium Complexes with Chiral Tetradentate PNNP Ligands in Asymmetric Catalytic Atom-Transfer Reactions. Curr Org Chem 2006;10:225-240.   DOI
19 Hamashima Y, Yagi K, Takano H, Tamas L, Sodeoka M. An efficient enantioselective fluorination of various beta-ketoesters catalyzed by chiral palladium complexes. J Am Chem Soc 2002;124:14530-14531.   DOI
20 Ma J-A, Cahard D. Copper(II) triflate-bis(oxazoline)- catalysed enantioselective electrophilic fluorination of ${\beta}$-ketoesters. Tetrahedron: Asymmetry 2004;15:1007-1011.   DOI
21 Ma J-A, Cahard D. Screening of chiral catalysts for enantioselective electrophilic fluorination of ${\beta}$-ketoesters. J Fluorine Chem 2004;125:1357-1361.   DOI
22 Huang D, Koren PR, Folting K, Davidson ER, Caulton KG. Facile and Reversible Cleavage of C−F Bonds. Contrasting Thermodynamic Selectivity for $Ru-CF_2H vs F-Os$ ═CFH. J Am Chem Soc 2000;122:8916-8931.   DOI
23 Akana JA, Bhattacharyya KX, Muller P, Sadighi JP. Reversible C−F bond formation and the Aucatalyzed hydrofluorination of alkynes. J Am Chem Soc 2007;129:7736-7737.   DOI
24 Hull KL, Anani WQ, Sanford MS. Palladium-catalyzed fluorination of carbon-hydrogen bonds. J Am Chem Soc 2006;128:7134-7135.   DOI
25 Yandulov DV, Tran NT. Aryl-fluoride reductive elimination from Pd(II): feasibility assessment from theory and experiment. J Am Chem Soc 2007;129:1342-1358.   DOI
26 Furuya T, Ritter T. Carbon−fluorine reductive elimination from a high-valent palladium fluoride. J Am Chem Soc 2008;130:10060-10061.   DOI
27 Furuya T, Kaiser HM, Ritter T. Palladium-mediated fluorination of arylboronic acids. Angew Chem Int Ed Engl. 2008;47:5993-5996.   DOI
28 Watson DA, Su M, Teverovskiy G, Zhang Y, García- Fortanet J, Kinzel T, Buchwald SL. Formation of ArF from LPdAr(F): catalytic conversion of aryl triflates to aryl fluorides. Science 2009;325:1661-1664.   DOI
29 Grushin VV, Marshall WJ. Ar−F Reductive Elimination from Palladium(II) Revisited. Organometallics 2007;26:4997-5002.   DOI
30 Bobbio C, Gouverneur V. Catalytic asymmetric fluorinations. Org Biomol Chem 2006;4:2065-2075.   DOI
31 Shibata N, Kohno J, Takai K, Shimaru T, Nakmura S, Toru T, Kanemasa S. Highly enantioselective catalytic fluorination and chlorination reactions of carbonyl compounds capable of two-point binding. Angew Chem Int Ed Engl. 2005;44:4204-4207.   DOI
32 Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M. Catalytic enantioselective fluorination of oxindoles. J Am Chem Soc 2005;127: 10164-10165.   DOI
33 Shibata N, Kohno J, Takai K, Shimaru T, Nakmura S, Toru T, Kanemasa, S. Highly enantioselective catalytic fluorination and chlorination reactions of carbonyl compounds capable of two-point binding. Angew Chem Int Ed Engl. 2005;44:4204-4207.   DOI
34 Lal GS, Pez GP, Syvret RG. Electrophilic NF Fluorinating Agents. Chem Rev 1996;96:1737-1756.   DOI
35 Deprez NR, Kalyani D, Krause A, Sanford MS. Room temperature palladium-catalyzed 2-arylation of indoles. J Am Chem Soc 2006;128:4972-4973.   DOI
36 Subramanian MA, Manzer LE. A "greener" synthetic route for fluoroaromatics via copper (II) fluoride. Science 2002;297:1665.   DOI
37 Janmanchi KM, Dolbier WR Jr. Highly Reactive and Regenerable Fluorinating Agent for Oxidative Fluorination of Aromatics. Org Process Res Dev 2008;12:349-354.   DOI
38 Dick AR, Sanford MS. Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds. Tetrahedron 2006;62:2439-2463.   DOI
39 Desai LV, Malik HA, Sanford MS. Oxone as an inexpensive, safe, and environmentally benign oxidant for C-H bond oxygenation. Org Lett 2006;8:1141-1144.   DOI
40 Dick AR, Kampf JW, Sanford MS. Unusually stable palladium(IV) complexes: detailed mechanistic investigation of C−O bond-forming reductive elimination. J Am Chem Soc 2005;127:12790-12791.   DOI
41 Ball ND, Sanford MS. Synthesis and reactivity of a monosigma- aryl palladium(IV) fluoride complex. J Am Chem Soc 2009;131:3796-3797.   DOI
42 Wang X, Mei T.-S, Yu J-Q. Versatile Pd(OTf)2 x 2 H2Ocatalyzed ortho-fluorination using NMP as a promoter. J Am Chem Soc 2009;131:7520-7521.   DOI
43 Kaspi AW, Yahav-Levi A, Goldberg I, Vigalok A. Xenon difluoride induced aryl iodide reductive elimination: a simple access to difluoropalladium(II) complexes. Inorg Chem 2008;47:5-7.   DOI
44 Furuya T, Strom AE, Ritter T. Silver-mediated fluorination of functionalized aryl stannanes. J Am Chem Soc 2009;131:1662-1663.   DOI
45 Grushin VV, Marshall WJ. Ar−F Reductive Elimination from Palladium(II) Revisited. Organometallics 2007;26:4997-5002.   DOI
46 Furuya T, Ritter T. Fluorination of boronic acids mediated by silver(I) triflate. Org Lett 2009;11:2860-2863.   DOI
47 Grushin VV. U.S. Patent 7202388, 2007.