Palladium-Catalyzed Intramolecular Fluorooxylation of Styrenes
Zheliang Yuan
State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorHaihui Peng
State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Guosheng Liu
State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925346; Fax: 0086-021-64166128Search for more papers by this authorZheliang Yuan
State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorHaihui Peng
State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Guosheng Liu
State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925346; Fax: 0086-021-64166128Search for more papers by this authorAbstract
A novel palladium-catalyzed intramolecular fluorooxylation of styrenes has been developed by using NFSI as fluorinating reagent. This reaction provides an efficient way for the synthesis of 2-aryl-3-fluorotetrahydrofuran derivatives.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
cjoc_201300437_sm_suppl.pdf805.5 KB | suppl |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1
Kirsch, P.,
Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004.
10.1002/352760393X Google Scholar
- 1b Purser, S. P.; Moore, R.; Swallow, S.; Gouverneur, V.. Chem. Soc. Rev., 2008, 37, 320.
- 2a
Welch, J. T.;
Eswarakrishnan, S.,
Fluorine in Bioorganic Chemistry, John Wiley, New York, NY, 1991.
10.1021/bk-1991-0456 Google Scholar
- 2b Uoto, K.; Ohsuki, S.; Takenoshita, H.; Ishiyama, T.; Iimura, S.; Hirota, Y.; Mitsui, I.; Terasawa, H.; Soga, T.. Chem. Pharm. Bull., 1997, 45, 1793.
- 2c Arimitsu, S.; Hammond, G. B.. J. Org. Chem., 2007, 72, 8559.
- 3a Wilkinson, S. C.; Lozano, O.; Schuler, M.; Pacheco, M.; Salmon, R.; Gouverneur, V.. Angew. Chem., Int. Ed., 2009, 48, 7083.
- 3b Wilkinson, S. C.; Salmon, R.; Gouverneur, V.. Future Med. Chem., 2009, 1, 847.
- 3c Lozano, O.; Blessley, G.; Martinez del Campo, T.; Thompson, A. L.; Giuffredi, G. T.; Bettati, M.; Walker, M.; Borman, R.; Gouverneur, V.. Angew. Chem., Int. Ed., 2011, 50, 8105.
- 3d Sawaguchi, M.; Hara, S.; Fukuhara, T.; Yoneda, N.. J. Fluorine Chem., 2000, 104, 277.
- 3e Okada, M.; Nakamura, Y.; Horikawa, H.; Inoue, T.; Taguchi, T.. J. Fluorine Chem., 1997, 82, 157.
- 3f Lourie, L. F.; Serguchev, Y. A.; Ponomarenko, M. V.; Rusanov, E. B.; Vovk, M. V.; Ignat′ev, N. V.. Tetrahedron, 2013, 69, 833.
- 4a Welch, J. T.. Tetrahedron, 1987, 43, 3123.
- 4b Inagaki, T.; Nakamura, Y.; Sawaguchi, M.; Yoneda, N.; Ayuba, S.; Hara, S.. Tetrahedron Lett., 2003, 44, 4117.
- 5For some recent reviews on transition metal-catalyzed fluorination, see:
- 5a Brown, J. M.; Gouverneur, V.. Angew. Chem., Int. Ed., 2009, 48, 8610.
- 5b Grushin, V. V.. Acc. Chem. Res., 2010, 43, 160.
- 5c Furuya, T.; Kamlet, A. S.; Ritter, T.. Nature, 2011, 473, 470.
- 5d Hopkinson, M. N.; Gee, A. D.; Gouverneur, V.. Isr. J. Chem., 2010, 50, 675.
- 5e Liu, G.. Org. Biomol. Chem., 2012, 10, 6243.
- 5f Lv, C.; Shen, Q.; Liu, D.. Chin. J. Org. Chem., 2012, 32, 1380 (in Chinese).
- 5g Qing, F.. Chin. J. Org. Chem., 2012, 32, 815 (in Chinese).
- 6 Hull, K. L.; Anani, W. Q.; Sanford, M. S.. J. Am. Chem. Soc., 2006, 128, 7134.
- 7 Tang, P.; Furuya, T.; Ritter, T.. J. Am. Chem. Soc., 2010, 132, 12150.
- 8a Akana, J. A.; Bhattacharyya, K. X.; Muller, P.; Sadighi, J. P.. J. Am. Chem. Soc., 2007, 129, 7736.
- 8b Schuler, M.; Silva, F.; Bobbio, C.; Tessier, A.; Gouverneur, V.. Angew. Chem., Int. Ed., 2008, 47, 7927.
- 8c de Haro, T.; Nevado, C.. Chem. Commun., 2011, 47, 248.
- 8d de Haro, T.; Nevado, C.. Adv. Synth. Catal., 2010, 352, 2767.
- 8e Qian, J.; Liu, Y.; Zhu, J.; Jiang, B.; Xu, Z.. Org. Lett., 2011, 13, 4220.
- 9a Wu, T.; Yin, G.; Liu, G.. J. Am. Chem. Soc., 2009, 131, 16354.
- 9b Qiu, S.; Xu, T.; Zhou, J.; Guo, Y.; Liu, G.. J. Am. Chem. Soc., 2010, 132, 2856.
- 9c Xu, T.; Mu, X.; Peng, H.; Liu, G.. Angew. Chem., Int. Ed., 2011, 50, 8176.
- 9d Peng, H.; Liu, G.. Org. Lett., 2011, 13, 772.
- 9e Xu, T.; Mu, X.; Peng, H.; Liu, G.. Chin. J. Chem., 2011, 29, 2785.
- 9f Peng, H.; Yuan, Z.; Wang, H.; Guo, Y.; Liu, G.. Chem. Sci., 2013, DOI: 10.1039/C3SC50690H
- XX Zhu, H.; Liu, G.. Acta Chim. Sinica, 2012, 70, 2404 (in Chinese).
- 10 The observation of poor diastereoselectivity from the reaction of E-1a possibly resulted from the facile oxidation of cis-2a.
- 11 The free F anion is possibly generated from the reaction of NFSI with Pd catalyst, for details, see reference 9d.
- 12 For details, see reference 9f.