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(3): 330-333
DOI: 10.1055/s-0032-1317847
DOI: 10.1055/s-0032-1317847
short paper
New, Efficient Approach for the Ligand-Free Suzuki–Miyaura Reaction of 5-Iodo-2′-deoxyuridine in Water
Further Information
Publication History
Received: 14 October 2012
Accepted after revision: 19 November 2012
Publication Date:
04 January 2013 (online)
Abstract
A series of 5-aryl-2′-deoxyuridines was prepared, using ligandless Suzuki–Miyaura cross-coupling reactions in neat water, starting from 5-iodo-2′-deoxyuridine as totally deprotected starting material. This ligand-free process gave good to high isolated yields within short reaction times and with low loadings of palladium.
-
References
- 1a Agrofoglio LA, Gillaizeau I, Saito Y. Chem. Rev. 2003; 103: 1875
- 1b Onuma S, Kumamoto H, Kawato M, Tanaka H. Tetrahedron 2002; 58: 2497
- 1c Haraguchi K, Itoh Y, Tanaka H, Akita M, Miyasaka T. Tetrahedron 1993; 49: 1371
- 1d Len C, Mackenzie G. Tetrahedron 2006; 62: 9085
- 1e Ewing DF, Fahmi N, Len C, Mackenzie G, Ronco G, Villa P, Shaw G. Nucleosides Nucleotides 1999; 18: 2613
- 1f Ewing DF, Fahmi N, Len C, Mackenzie G, Pranzo A. J. Chem. Soc., Perkin Trans. 1 2000; 3561
- 1g Lipka-Belloli E, Len C, Mackenzie G, Ronco G, Bonte JP, Vaccher C. J. Chromatogr., A 2001; 943: 91
- 1h Ewing DF, Len C, Mackenzie G, Ronco G, Villa P. Tetrahedron: Asymmetry 2000; 11: 4995
- 1i Selouane A, Vaccher C, Villa P, Postel D, Len C. Tetrahedron: Asymmetry 2002; 13: 407
- 1j Pilard S, Riboul D, Glacon V, Moitessier N, Chapleur Y, Postel D, Len C. Tetrahedron: Asymmetry 2002; 13: 529
- 1k Egron D, Périgaud C, Gosselin G, Aubertin A.-M, Faraj A, Sélouane M, Postel D, Len C. Bioorg. Med. Chem. Lett. 2003; 13: 4473
- 2 Pesnot T, Wagner GK. Org. Biomol. Chem. 2008; 6: 2884
- 3 Segal M, Fischer B. Org. Biomol. Chem. 2012; 10: 1571
- 4 Naus P, Pohl R, Votruba I, Dzubak P, Hajduch M, Ameral R, Birkus G, Wang T, Ray AS, Mackman R, Cihlar T, Hocek M. J. Med. Chem. 2010; 53: 460
- 5 Fukuda M, Nakamura M, Takada T, Yamana K. Tetrahedron Lett. 2010; 51: 1732
- 6 Jacobsen MF, Ferapontova EE, Gothelf KV. Org. Biomol. Chem. 2009; 7: 905
- 7 Wanninger-Weiß C, Wagenknecht H.-A. Eur. J. Org. Chem. 2008; 64
- 8 Ehrenschwender T, Wagenknecht H.-A. Synthesis 2008; 3657
- 9 Capobianco ML, Cazzato A, Alesi S, Barbarella G. Bioconjugate Chem. 2008; 19: 171
- 10 Okamoto A, Tainaki K, Unzai T, Saito I. Tetrahedron 2007; 63: 3465
- 11 Okamoto A, Inasaki T, Saito I. Tetrahedron Lett. 2005; 46: 791
- 12 Greco NJ, Tor Y. J. Am. Chem. Soc. 2005; 127: 10784
- 13 Hubert R, Fiebig T, Wagenknecht H.-A. Chem. Commun. 2003; 1878
- 14 Amann N, Wagenknecht H.-A. Synlett 2002; 687
- 15 Amann N, Pandurski E, Fiebig T, Wagenknecht H.-A. Chem. Eur. J. 2002; 8: 4877
- 16 Amann N, Pandurski E, Fiebig T, Wagenknecht H.-A. Angew. Chem. Int. Ed. 2002; 41: 2978
- 17 Aucagne V, Berteina-Raboin S, Guenot P, Agrofoglio LA. J. Comb. Chem. 2004; 6: 717
- 18 El Kazzouli S, Berteina-Raboin S, Agrofoglio LA. Nucleosides, Nucleotides Nucleic Acids 2007; 26: 1398
- 19 Yamamoto Y, Seko T, Nemoto H. J. Org. Chem. 1989; 54: 4734
- 20 Sadler JM, Ojewoye O, Seley-Radtke KL. Nucleic Acids Symp. Ser. 2008; 52: 571
- 21 Srivatsan SG, Tor T. J. Am. Chem. Soc. 2007; 129: 2044
- 22 Peyron C, Benhida R, Bories C, Loiseau PM. Bioorg. Chem. 2005; 33: 439
- 23 Wüst FR, Kniess T. J. Labelled Compd. Radiopharm. 2004; 47: 457
- 24 Haouz A, Vanheusden V, Munier-Lehmann H, Froeyen M, Herdewijn P, Van Calenbergh S, Delarue M. J. Biol. Chem. 2003; 278: 4963
- 25 Netzel TL, Zhao M, Nafisi K, Headrick J, Sigman MS, Eaton BE. J. Am. Chem. Soc. 1995; 117: 9119
- 26 Gutierrez AJ, Terhost TJ, Matteucci MD, Froehler BC. J. Am. Chem. Soc. 1994; 116: 5540
- 27 Wigerinck P, Kerremans L, Claes P, Snoeck R, Maugdal P, De Clercq E, Herdewijn P. J. Med. Chem. 1993; 36: 538
- 28 Hassan ME. Collect. Czech. Chem. Commun. 1991; 56: 1944
- 29 Crips GT, Flynn BL. Tetrahedron Lett. 1990; 31: 1347
- 30 Saughnessy KH. Chem. Rev. 2009; 109: 643
- 31a Del Zotto A, Amoroso F, Baratta W, Rigo P. Eur. J. Org. Chem. 2009; 110
- 31b de Souza AL. F, Silva AD. C, Antunes OA. C. Appl. Organomet. Chem. 2009; 23: 5
- 31c Silva AD. C, Senra JD, Aguiar LC. S, Simas AB. C, de Souza AL. F, Malta LF. B, Antunes OA. C. Tetrahedron Lett. 2010; 51: 3883
- 31d Qiu J, Wang L, Liu M, Shen Q, Tang J. Tetrahedron Lett. 2011; 52: 6489
- 31e Alimardanov A, Schmieder-van de Vonderwoort L, de Vries AH. M, de Vries JG. Adv. Synth. Catal. 2004; 346: 1812
- 31f de Vries JG, de Vries AH. M. Eur. J. Org. Chem. 2003; 799
- 31g Hu H, Ge C, Zhang A, Ding L. Molecules 2009; 14: 3153
- 32a Polshettivar V, Decottignies A, Len C, Fihri A. ChemSusChem 2010; 3: 502
- 32b Fihri A, Luart D, Len C, Solhy A, Chevrin C, Polshettivar V. Dalton Trans. 2011; 40: 3116
- 33 Riedl J, Pohl R, Rulisek L, Hocek M. J. Org. Chem. 2012; 77: 1026
- 34 Kogler M, Vanderhoydonck B, De Jonghe S, Rozenski J, Van Belle K, Herman J, Louat T, Parchina A, Sibley C, Lescrinier E, Herdewijn P. J. Med. Chem. 2011; 54: 4847
- 35 Shih YC, Chien TC. Tetrahedron 2011; 67: 3915
- 36 Kalachova L, Pohl R, Hocek M. Synthesis 2009; 105
- 37 Mizuta M, Banba J.-i, Kanamori T, Ohkubo A, Sekine M, Seio K. Nucleic Acids Symp. Ser. 2007; 51: 25
- 38 Čapek P, Cahová H, Pohl R, Hocek M, Gloeckner C, Marx A. Chem. Eur. J. 2007; 13: 6196
- 39 Wagner C, Wagenknecht H.-A. Chem. Eur. J. 2005; 11: 1871
- 40 Western EC, Daft JR, Johnson EM, Gannett PM, Shaughnessy KH. J. Org. Chem. 2003; 68: 6767
- 41 Sartori G, Enderlin G, Hervé G, Len C. Synthesis 2012; 44: 767
- 42 Lawson Daku KM, Newton RF, Pearce SP, Vile J, Williams JM. J. Tetrahedron Lett. 2003; 44: 5095