Introduction
Aryl fluorides display unique chemical, physical, and pharmaceutical properties such as increased metabolic stability, solubility, and bioavailability [1, 2]. Functionalized aryl fluorides are wildly used in the fields of materials [3, 4], pharmaceuticals [5, 6], agrochemicals [7, 8], and position emission tomography (PET) [9, 10]. Although many researches have been done, the formation of aromatic C–F bond is still more challenging compared to the formation of other carbon–halogen bond [9, 11, 12]. Traditional methods to construct aryl fluorides such as nucleophilic aromatic substitution and Balz-Schiemann reaction often require harsh reaction conditions and are limited to narrow substrate scopes. In nucleophilic aromatic substitution, only electron-deficient aromatics can give good to well yields. And the tetrafluoroborate salts used in Balz-Schiemann are potentially explosive species and not easy to be prepared in mild conditions [13, 14, 15].
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References
Cametti M, Crousse B, Metrangolo P, Milani R, Resnati G (2012) The fluorous effect in biomolecular applications. Chem Soc Rev 41: 31–42
O’Hagan D (2008) Understanding organofluorine chemistry. An introduction to the C–F bond. Chem Soc Rev 37: 308–319
Berger R, Resnati G, Metrangolo P, Weber E, Hulliger J (2011) Organic fluorine compounds: a great opportunity for enhanced materials properties. Chem Soc Rev 40: 3496–3508
Babudri F, Farinola GM, Naso F, Ragni R (2007) Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom. Chem Commun 2007: 1003–1022
Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA (2015) Applications of fluorine in medicinal chemistry. J Med Chem 58: 8315–8359
Purser S, Moore PR, Swallow S, Gouverneur V (2008) Fluorine in medicinal chemistry. Chem Soc Rev 37: 320–330
Fujiwara T, O’Hagan D (2014) Successful fluorine-containing herbicide agrochemicals. J Fluorine Chem 167: 16–29
Jeschke P (2004) The unique role of fluorine in the design of active ingredients for modern crop protection. ChemBioChem 5: 570–589
Preshlock S, Tredwell M, Gouverneur V (2016) 18F-Labeling of arenes and heteroarenes for applications in positron emission tomography. Chem Rev 116: 719–766
Tredwell M, Gouverneur V (2012) 18F-Labeling of arenes. Angew Chem Int Ed 51:11426–11437
Campbell MG, Ritter T (2014) Modern carbon–fluorine bond forming reactions for aryl fluoride synthesis. Chem Rev 115: 612–633
Furuya T, Klein JE, Ritter T (2010) Carbon–fluorine bond formation for the synthesis of aryl fluorides. Synthesis 2010:1804–1821
Balz G, Schiemann G (1927) Über aromatische fluoroverbindungen, I.: ein neues varfahren zu ihrer darstellung. Ber Dtsch Chem Ges B 60: 1186−1190
Adams D, Clark J (1999) Nucleophilic routes to selectively fluorinated aromatics. Chem Soc Rev 28: 225–231
Laali KK, Gettwert VJ (2001). Fluorodediazoniation in ionic liquid solvents: new life for the Balz–Schiemann reaction. J Fluorine Chem 107: 31–34
Alvarez-Corral M, Munoz-Dorado M, Rodriguez-Garcia I (2008) Silver-mediated synthesis of heterocycles. Chem Rev 108: 3174–3198
Fang G, Bi X (2015) Silver-catalysed reactions of alkynes: recent advances. Chem Soc Rev 44: 8124–8173
Naodovic M, Yamamoto H (2008) Asymmetric silver-catalyzed reactions. Chem Rev 108: 3132–3148
Tius MA, Kawakami JK (1992). Vinyl fluorides from vinyl stannanes. Synthetic Commun 22: 1461–1471
Tius MA, Kawakami JK (1993) Rapid fluorination of alkenyl stannanes with silver triflate and xenon difluoride. Synlett 1993: 207–208
Tius MA, Kawakami, JK (1995) The reaction of XeF2 with trialkylvinylstannanes: scope and some mechanistic observations. Tetrahedron 51: 3997–4010
Stille JK (1986) The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles [new synthetic methods (58)]. Angew Chem Int Ed Engl 25: 508–524
Beverwijk CDM, Van der Kerk G JM (1972) The synthesis and properties of phenylsilver. J Organometallic Chem 43: 7–10.
Krause E, Schmitz M (1919) Gemischte blei- und zinn-aryle und -aryl-alkyl und ihre verwendung zur darstellung von silber-organoverbindungen, zugleich beispiele für den einfluß des symmetriegrades auf die eigenschaften chemischer verbindungen. Ber Dtsch Chem Ges 52: 2150–2164
Furuya T, Strom AE, Ritter T (2009) Silver-mediated fluorination of functionalized aryl stannanes. J Am Chem Soc 131: 1662–1663
Tang P, Furuya T, Ritter, T. (2010). Silver-catalyzed late-stage fluorination. J Am Chem Soc 132: 12150–12154
Teare H, Robins EG, Kirjavainen A, Forsback S, Sandford G, Solin O, Luthra SK, Gouverneur V. (2010). Radiosynthesis and evaluation of [18F]Selectfluor bis(triflate). Angew Chem Int Ed 49: 6821–6824
Stenhagen IS, Kirjavainen AK, Forsback SJ, Jørgensen CG, Robins EG, Luthra SK, Solin O, Gouverneur, V (2013) [18F]Fluorination of an arylboronic ester using [18F]selectfluor bis(triflate): application to 6-[18F]fluoro-L-DOPA. Chem Commun 49: 1386–1388
Lennox AJ, Lloyd-Jones GC (2014) Selection of boron reagents for Suzuki–Miyaura coupling. Chem Soc Rev 43: 412–443
Furuya T, Ritter T (2009) Fluorination of boronic acids mediated by silver (I) triflate. Org Lett 11: 2860–2863
Dubbaka SR, Narreddula VR, Gadde S, Mathew T (2014) Silver-mediated fluorination of potassium aryltrifluoroborates with Selectfluor®. Tetrahedron 70: 9676–9681
Nakao Y, Hiyama T (2011) Silicon-based cross-coupling reaction: an environmentally benign version. Chem Soc Rev 40: 4893–4901
Denmark SE, Sweis RF (2002) Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon–oxygen bonds. Acc. Chem. Res. 35: 835–846
Tang P, Ritter T (2011) Silver-mediated fluorination of aryl silanes. Tetrahedron 67: 4449–4454
Van Der Puy, M. (1987). Direct fluorination of substituted pyridines. Tetrahedron Lett 28 255–258
Chambers RD, Parsons M, Sandford G, Skinner CJ, Atherton MJ, Moilliet JS (1999) Elemental fluorine. Part 10.1 Selective fluorination of pyridine, quinoline and quinoxaline derivatives with fluorine–iodine mixtures. J Chem Soc Perkin Trans 1: 803–810
Zweig A, Fischer RG, Lancaster JE (1980) New method for selective monofluorination of aromactics using silver difluoride. J Org Chem 1980: 3597–3603
Fier PS, Hartwig JF (2013) Selective C–H fluorination of pyridines and diazines inspired by a classic amination reaction. Science 342: 956–960
Fier PS, Hartwig JF (2014) Synthesis and late-stage functionalization of complex molecules through C–H fluorination and nucleophilic aromatic substitution. J Am Chem Soc 136: 10139–10147
Wang C, Cai J, Zhang M, Zhao X (2017) Ag-assisted fluorination of unprotected 4,6-disubstituted 2-aminopyrimidines with Selectfluor. J Org Chem 82: 1260–1265
Kober E, Schroeder H, RÄtz RFW, Ulrich H, Grundmann C (1961) Synthesis of polyfluorinated heterocycles by indirect fluorination with silver fluorides. I. fluoro-s-triazines and reactions of cyanuric fluoride. J Org Chem 27: 2577–2580
Schroeder H, Kober E, Ulrich H, RÄtz R, Agahigian H, Grundmann C (1961) Synthesis of polyfluorinated heterocycles by indirect fluorination with silver fluorides. II. fluoropyrimidines. J Org Chem 27: 2580–2584
Ulrich H, Kober E, Schroeder H, RÄtz R, Grundmann C (1961) Synthesis of polyfluorinated heterocycles by indirect fluorination with silver fluorides. III. fluoropiperideines, fluoropyrrolines, and fluoropyrrolenine. J Org Chem 27: 2585–2589
Schroeder H, RÄtz R, Schnabel W, Ulrich H, Kober E, Grundmann C (1961) Synthesis of polyfluorinated heterocycles by indirect fluorination with silver fluorides. IV. Fluorothiadiazoles. J Org Chem 27: 2589–2592
Ulrich H, Kober E, RÄtz R, Schroeder H, Grundmann C (1961) Synthesis of polyfluorinated heterocycles by indirect fluorination with silver fluorides. V. fluorothiophene. J Org Chem 27: 2593–2595
Font M, Acuña-Parés F, Parella T, Serra J, Luis JM, Lloret-Fillol J, Costas M, Ribas X (2014) Direct observation of two-electron Ag(I)/Ag(III) redox cycles in coupling catalysis. Nat Commun 5: 4373–4383
Wang D, Sun W, Chu T (2015) Synthesis of 5-fluorotriazoles by silver-mediated fluorination of 5-iodotriazoles. Eur J Org Chem 2015: 4114–4118
Worrell BT, Hein JE, Fokin VV (2012) Halogen exchange (halex) reaction of 5-iodo-1,2,3-triazoles: synthesis and applications of 5-fluorotriazoles. Angew Chem Int Ed 51: 11791–11794
Liu Q, Yuan Z, Wang H Y, Li Y, Wu Y, Xu T, Leng X. Chen P, Guo Y, Lin Z, Liu, G. (2015). Abnormal mesoionic carbene silver complex: synthesis, reactivity, and mechanistic insight on oxidative fluorination. ACS Catal 5: 6732–6737
Xu T, Wu Y, Yuan Z, Guan H, Liu G (2016) Mechanistic investigation on the silver-catalyzed oxidative intramolecular aminofluorination of alkynes. Organometallics 35: 1347–1349
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Xu, P., Pingping, T. (2020). Silver-Mediated Fluorination for Preparing Aryl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-3896-9_9
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