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Aliphatic [18F]Fluorination Chemistry for Positron Emission Tomography Read chapter Read first chapter

2020 | OriginalPaper | Chapter

Copper-Mediated Fluorination for Preparing Aryl Fluorides

Authors : Wenjun Miao, Jinbo Hu

Published in: Fluorination

Publisher: Springer Singapore

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Excerpt

Functionalized aryl fluorides are important motifs because of their widespread application in pharmaceuticals, agrochemicals, materials, and medical diagnosis (positron emission tomography, PET) [1]. As a result, the development of efficient and practical procedures for the construction of aryl C–F bonds has received much attention. Recently, a series of transition metals have been explored for preparing aryl fluorides [2, 3]. Inexpensive metals such as copper have emerged as alternative mediators of C−F bond formation [4]. This section mainly focused on recent advances in copper-mediated/-catalyzed fluorination reactions to construct aryl fluorides. Among these reactions, the fluoride sources could be divided into nucleophilic fluorinating reagents and electrophilic fluorinating reagents (Scheme 1). …

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previous chapter Chemistry of BrF3 Constructing the CF2, CF3 and CF2H Groups
next chapter Copper-Mediated Nucleophilic Fluorination for Preparing Alkyl Fluorides
Literature
1.
(a) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. (b) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305. (c) Müller, K.; Faeh, C.; Diederich, F. Science2007, 317, 1881. (d) Josse, O.; Labar, D.; Georges, B.; Gregoire, V.; Marchand-Brynaert, J. Bioorg. Med. Chem. 2001, 9, 665. (e) Miller, P. W.; Long, N. J.; Vilar, R.; Gee, A. D. Angew. Chem. Int. Ed. 2008, 47, 8998. (f) Ametamey, S. M.; Honer, M.; Schubiger, P. A. Chem. Rev. 2008, 108, 1501. (g) Tredwell, M.; Gouverneur, V. Angew. Chem. Int. Ed. 2012, 51, 11426.
2.
For silver-mediated or -catalyzed aromatic fluorination, see: (a) Furuya, T.; Strom, A. E.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 1662. (b) Tang, P.; Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 12150. (c) Furuya, T.; Ritter, T. Org. Lett. 2009, 11, 2860.
3.
For palladium-mediated or -catalyzed aromatic fluorination, see: (a) Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 10060. (b) Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; García-Fortanet,J.; Kinzel, T.; Buchwald, S. L. Science2009, 325, 1661. (c) Noël, T.; Maimone, T. J.; Buchwald, S. L. Angew. Chem. Int. Ed. 2011, 50, 8900. (d) Mazzotti, A. R.; Campbell, M. G.; Tang, P.; Murphy, J. M.; Ritter, T. J. Am. Chem. Soc. 2013, 135, 14012. (e) Lee, H. G.; Milner, P. J.; Buchwald, S. L. Org. Lett. 2013, 15, 5602. (f) Lee, H. G.; Milner, P. J.; Buchwald, S. L. J. Am. Chem. Soc. 2014, 136, 3792.
4.
Mu, X.; Liu, G. Org. Chem. Front. 2014, 1, 430.
5.
6.
Mu, X.; Zhang, H.; Chen, P.; Liu, G. Chem. Sci.2014, 5, 275.
7.
For reviews on diaryliodonium salts, see: (a) Zhdankin, V. V. Chem. Rev.2002, 102, 2523. (b) Deprez, N. R.; Sanford, M. S. Inorg. Chem.2007, 46, 1924. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299. (d) Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed.2009, 48, 9052.
8.
For selected examples, see: (a) Jalalian, N.; Ishikawa, E. E.; Silva, L. F.; Olofsson, B. Org. Lett.2011, 13, 1552. (b) Laudge, K. P.; Jang, K. S.; Lee, S. Y.; Chi, D. Y. J. Org. Chem.2012, 77, 5705. (c) Umierski, N.; Manolikakes, G. Org. Lett.2013, 15, 188. (d) Wagner, A. M.; Sanford, M. S. J. Org. Chem.2014, 79, 2263.
9.
For selected examples, see: (a) Lv, T.; Wang, Z.; You, J.; Lan, J.; Gao, G. J. Org. Chem. 2013, 78, 5723. (b) Cullen, S. C.; Shekhar, S.; Nere, N. K. J. Org. Chem. 2013, 78, 12194. (c) Sokolovs, I.; Lubriks, D.; Suna, E. J. Am. Chem. Soc. 2014, 136, 6920. (d) Fañanás-Mastral, M.; Feringa, B. L. J. Am. Chem. Soc. 2014, 136, 9894.
10.
(a) Ichiishi, N.; Canty, A. J.; Yates, B. F.; Sanford, M. S. Org. Lett.2013, 15, 5134. (b) Ichiishi, N.; Canty, A. J.; Yates, B. F.; Sanford, M. S. Organometallics2014, 33, 5525.
11.
12.
13.
Ye, Y.; Schimler, S. D.; Hanley, P. S.; Sanford, M. S. J. Am. Chem. Soc. 2013, 135, 16292.PubMed
14.
Gamache, R. F.; Waldmann, C.; Murphy, J. M. Org. Lett.2016, 18, 4522.PubMed
15.
16.
(a) Cai, L.; Lu, S.; Pike, V. W. Eur. J. Org. Chem. 2008, 2853. (b) Ametamey, S. M.; Honer, M.; Schubiger, P. A. Chem. Rev. 2008, 108, 1501. (c) Littich, R.; Scott, P. J. H. Angew. Chem., Int. Ed. 2012, 51, 1106.
17.
Preshlock, S.; Tredwell, M.; Gouverneur, V. Chem. Rev. 2016, 116, 719.PubMed
18.
(a) Ichiishi, N.; Brooks, A. F.; Topczewski, J. J.; Rodnick, M. E.; Sanford, M. S.; Scott, P. J. H. Org. Lett.2014, 16, 3224. (b) Mossine, A. V.; Brooks, A. F.; Makaravage, K. J.; Miller, J. M.; Ichiishi, N.; Sanford, M. S.; Scott, P. J. H. Org. Lett.2015, 17, 5780. (c) Tredwell, M.; Preshlock, S. M.; Taylor, N. J.; Gruber, S.; Huiban, M.; Passchier, J.; Mercier, J.; Génicot, C.; Gouverneur, V. Angew. Chem., Int. Ed. 2014, 53, 7751. (d) Taylor, N. J.; Emer, E.; Preshlock, S.; Schedler, M.; Tredwell, M.; Verhoog, S.; Mercier, J.; Genicot, C.; Gouverneur, V. J. Am. Chem. Soc. 2017, 139, 8267.
Metadata
Title
Copper-Mediated Fluorination for Preparing Aryl Fluorides
Authors
Wenjun Miao
Jinbo Hu
Copyright Year
2020
Publisher
Springer Singapore
Book
Fluorination

Print ISBN: 978-981-10-3895-2

Electronic ISBN: 978-981-10-3896-9

Copyright Year: 2020

DOI
https://doi.org/10.1007/978-981-10-3896-9_63

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