Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(22): 3157-3163
DOI: 10.1055/s-0033-1339668
DOI: 10.1055/s-0033-1339668
paper
Synthesis and Properties of α-Bromomethyl-Substituted β-Ethoxyvinyl Polyfluoroalkyl Ketones
Further Information
Publication History
Received: 14 May 2013
Accepted after revision: 02 August 2013
Publication Date:
29 August 2013 (online)

Abstract
An efficient and practical method for the synthesis of α-bromomethyl-substituted β-alkoxyvinyl polyfluoroalkyl ketones is reported. These highly functionalized α-bromomethyl enones easily react with various nucleophiles and binucleophiles affording a wide variety of new functionalized enones and heterocyclic systems that are perspective starting materials for the synthesis of compounds with potentially high biological and pharmacological activity.
Key words
enones - fluorine - halogenation - radical reaction - nucleophilic reaction - heterocyclesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Begue J.-P, Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine . Wiley; Hoboken: 2008
- 2a Böhm H.-J, Banner D, Bendels S, Kansy M, Kuhn B, Müller K, Obst-Sander U, Stahl M. ChemBioChem 2004; 5: 637
- 2b O’Hagan D. J. Fluorine Chem. 2010; 131: 1071
- 2c Hagmann WK. J. Med. Chem. 2008; 51: 4359
- 3a Nagib DA, MacMillan DW. C. Nature 2011; 480: 224
- 3b Vorbrüggen H. Helv. Chim. Acta 2011; 94: 947
- 3c Grygorenko OO, Artamonov OS, Komarov IV, Mikhaylyuk PK. Tetrahedron 2011; 67: 803
- 3d Acena JL, Sorochinsky AE, Soloshonok VA. Synthesis 2012; 44: 1591
- 4a Litvinas ND, Fier PS, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 536
- 4b Parsons AT, Buchwald SL. Angew. Chem. Int. Ed. 2011; 50: 9120
- 4c Jiang X, Chu L, Qing F.-L. J. Org. Chem. 2012; 77: 1251
- 4d Wang X, Ye Y, Zhang S, Feng J, Xu Y, Zhang Y, Wang J. J. Am. Chem. Soc. 2011; 133: 16410
- 4e Barker TJ, Boger DL. J. Am. Chem. Soc. 2012; 134: 13588
- 4f Zanardi A, Novikov MA, Martin E, Benet-Bucholz J, Grushin VV. J. Am. Chem. Soc. 2011; 133: 20901
- 4g Artamonov OS, Slobodyanyuk EY, Shishkin OV, Komarov IV, Mikhaylyuk PK. Synthesis 2013; 45: 0225
- 4h Fujikawa K, Kobayashi A, Amii H. Synthesis 2012; 44: 3015
- 5a Sevenard DV, Kazakova O, Schoth R.-M, Lork E, Röschenthaler G.-V. J. Chem. Crystallogr. 2011; 41: 1795
- 5b Loop I, Skarpos H, Kalinovich N, Kazakova O, Lork E, Röschenthaler G.-V. J. Fluorine Chem. 2010; 131: 389
- 5c Sevenard DV, Vorobyev M, Sosnovskikh VYa, Wessel H, Kazakova O, Vogel V, Shevchenko NE, Nenajdenko VG, Lork E, Röschenthaler G.-V. Tetrahedron 2009; 65: 7538
- 5d Irgashev RA, Sosnovskikh VYa, Kalinovich N, Kazakova O, Röschenthaler G.-V. Tetrahedron Lett. 2009; 50: 4903
- 5e Sevenard DV, Kazakova O, Schoth R.-M, Lork E, Chizhov DL, Poveleit J, Röschenthaler G.-V. Synthesis 2008; 1867
- 5f Sevenard DV, Kazakova O, Lork E, Duelcks T, Chizhov DL, Röschenthaler G.-V. J. Mol. Struct. 2007; 846: 87
- 5g Tolmachova NA, Dolovanyuk VG, Gerus II, Kondratov IS, Polovinko VV, Bergander K, Haufe G. Synthesis 2011; 1149
- 5h Tolmacheva NA, Gerus II, Dolovanyuk VG, Kondratov IS, Haufe G. Eur. J. Org. Chem. 2009; 5012
- 5i Kondratov IS, Dolovanyuk VG, Tolmachova NA, Gerus II, Bergander K, Fröhlich R, Haufe G. Org. Biomol. Chem. 2012; 10: 8778
- 6a Zhu SZ, Wang YL, Peng WM, Song LP, Jin GF. Curr. Org. Chem. 2002; 6: 1057
- 6b Schoth RM, Sevenard D, Pashkevich K, Röschenthaler G.-V. Coord. Chem. Rev. 2000; 210: 101
- 7a Nenajdenko VG, Sanin AV, Balenkova ES. Russ. Chem. Rev. 1999; 68: 483
- 7b Druzhinin SV, Balenkova ES, Nenajdenko VG. Tetrahedron 2007; 63: 7753
- 8a Song T, Zhao J, Jiang H, Zhu S, Liu L, Xu L. Tetrahedron 2012; 68: 5677
- 8b Chopin N, Decamps S, Gouger A, Medebielle M, Picot S, Bienvenu A.-L, Pilet G. J. Fluorine Chem. 2011; 132: 850
- 8c Xin Y, Zhao J, Zhu S. J. Fluorine Chem. 2012; 133: 98
- 8d Kim MS, Ryu H, Kang DW, Cho S.-H, Seo S, Park YS, Kim M.-Y, Kwak EJ, Kim YS, Bhondwe RS, Kim HS, Lee J, Park S.-G, Son K, Choi S, Deandrea-Lazarus IA, Pearce LV, Blumberg PM, Frank R, Bahrenberg G, Stockhausen H, Koegel BY, Schiene K, Christoph T. J. Med. Chem. 2012; 55: 8392
- 8e Nunes CM, Ramos Silva M, Matos Beja A, Fausto R, Pinho e Melo TM. V. D. Tetrahedron Lett. 2010; 51: 411
- 8f Chopin N, Medebielle M, Pilet G. Eur. J. Inorg. Chem. 2012; 1093
- 8g Baharfar R, Azimi R. Chin. Chem. Lett. 2011; 22: 1183
- 8h Tolmachova NA, Gerus II, Vdovenko SI, Haufe G, Kirzhner YA. Synthesis 2007; 3797
- 9a Gerus II, Kacharova LM, Vdovenko SI. Synthesis 2001; 431
- 9b Volle J.-N, Schlosser M. Eur. J. Org. Chem. 2002; 1490
- 10a Rulev AYu, Fedorov SV, Nenajdenko VG, Balenkova ES, Voronkov MG. Russ. Chem. Bull. 2003; 52: 2287
- 10b Fedorov SV, Rulev AYu, Chipanina NN, Shulunova AM, Nenajdenko VG, Balenkova ES, Tyurin DA, Turchaninov VK. Russ. Chem. Bull. 2005; 54: 103
- 10c Nenajdenko VG, Reznichenko AL, Balenkova ES. Russ. Chem. Bull. 2006; 55: 172
- 10d Kacharova LM, Gerus II, Kacharov AD. J. Fluorine Chem. 2002; 117: 193
- 11a Shaitanova EN, Gerus II, Kukhar VP. Tetrahedron Lett. 2008; 49: 1184
- 11b Tarasenko KV, Gerus II, Kukhar VP. J. Fluorine Chem. 2007; 128: 1264
- 11c Tarasenko KV, Kukhar VP, Gerus II, Manoylenko OV, Röschenthaler G.-V. Tetrahedron Lett. 2010; 51: 4623
- 11d Zanatta N, Schneider JM. F. M, Schneider PH, Wouters AD, Bonacorso HG, Martins MA. P, Wessjohann LA. J. Org. Chem. 2006; 71: 6996
- 11e Martins MA. P, Sinhorin AP, Rosa A, Flores AF. C, Wastowski AD, Pereira CM. P, Flores DC, Beck P, Freitag RA, Brondani S, Cunico W, Bonacorso HG, Zanatta N. Synthesis 2002; 2353
- 11f Tarasenko KV, Gerus II, Kukhar VP, Polovinko VV. Collect. Czech. Chem. Commun. 2009; 74: 335
- 11g Zanatta N, Flores DC, Madruga CC, Flores AF. C, Bonacorso HG, Martins MA. P. Tetrahedron Lett. 2006; 47: 573
- 11h Zanatta N, Flores DC, Amaral SS, Bonacorso HG, Martins MA. P, Flores AF. C. Synlett 2005; 3079
- 12a Hojo M, Masuda R, Okada E, Sakaguchi S, Narumiya H, Morimoto K. Tetrahedron Lett. 1989; 30: 6173
- 12b Mamat C, Pundt T, Schmidt A, Langer P. Tetrahedron Lett. 2006; 47: 2183
- 12c Colla A, Martins MA. P, Clar G, Krimmer S, Fischer P. Synthesis 1991; 483
- 12d Bravo P, Bruche L, Farina A, Gerus II, Kolytcheva MT, Kukhar VP, Meille SV, Viani F. J. Chem. Soc., Perkin Trans. 1 1995; 1667
- 13 Martins MA. P, Sinhorin AP, Zimmermann NE. K, Zanatta N, Bonacorso HG, Bastos GP. Synthesis 2001; 1959
- 14a Gorbunova MG, Gerus II, Galushko SV, Kukhar VP. Synthesis 1991; 207
- 14b Buback M, Tost W, Hübsch T, Voss E, Tietze LF. Chem. Ber. 1989; 122: 1179
- 14c Sanin AV, Nenajdenko VG, Smolko KI, Denisenko DI, Balenkova ES. Synthesis 1998; 842
- 14d Gerus II, Gorbunova MG, Vdovenko SI, Yagupol’skii YuL, Kukhar VP. Zh. Org. Khim. 1990; 26: 1877
- 14e Okada E, Masuda R, Hojo M, Inoue R. Synthesis 1992; 533
- 15a Pradère J.-P, Roze JC, Quinion H, Danion-Bougot R, Danion D, Toupet L. Can. J. Chem. 1986; 64: 597
- 15b Tuloup R, Danion-Bougot R, Danion D, Pradère J.-P, Toupet L. Can. J. Chem. 1989; 67: 1125
- 16 Crystallographic data for compound 14 have been deposited with the accession number CCDC 932863 and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
Some recent reviews, see
For some recent examples, see:
Reviews on fluorinated enones and enaminones:
Some recent articles, see: