A ligand-free solid-supported system for Sonogashira couplings: Applications in nucleoside chemistry

Chemical Communications

Volumn , Issue 36, 2005, Pages 4551-4553

  Garg, Neil K ^a   Woodroofe, Carolyn C ^a   Lacenere, Christopher J ^b   Quake, Stephen R ^c,d   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^c California Institute of Technology   (United States)

^d Stanford University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (2 BROMOVINYL) 2' DEOXYURIDINE; ANTIHERPETIC AGENT; ANTIVIRUS AGENT; DEOXYURIDINE; LIGAND; NUCLEOSIDE DERIVATIVE; POLACRILIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CROSS COUPLING REACTION; DNA SEQUENCE; DRUG PURIFICATION; DRUG SYNTHESIS; HECK REACTION; SONOGASHIRA REACTION;

EID: 26444431760     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b505737j     Document Type: Article

References (34)

1. (a) Metal-Catalyzed Cross-Coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998;
2. (b) H. Geissler, in Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm, Wiley-VCH, Weinheim, 1998, vol. 1, ch. 2.10, p. 158;
3. (c) J. Tsuji, Transition Metal Reagents and Catalysts, Wiley, Chichester, U.K., 2000, ch. 3, p. 27.
4. (a) K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 16, 4467;
5. (b) K. Sonogashira, Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 3, ch. 2.4, p. 521, and references therein;
6. (c) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya and I. P. Beletskaya, Tetrahedron Lett., 1996, 37, 897;
7. (d) T. Hundertmark, A. F. Littke, S. L. Buchwald and G. C. Fu, Org. Lett., 2000, 2, 1729;
8. (e) M. Erdélyi and A. Gogoll, J. Org. Chem., 2001, 66, 4165.
9. For a pertinent review, see: L. A. Agrofoglio, I. Gillaizeau and Y. Saito, Chem. Rev., 2003, 103, 1875.
10. J. M. Prober, G. L. Trainor, R. J. Dam, F. W. Hobbs, C. W. Robertson, R. J. Zagursky, A. J. Cocuzza, M. A. Jensen and K. Baumeister, Science, 1987, 238, 336.
11. I. Braslavsky, B. Hebert, E. Kartalov and S. R. Quake, Proc. Natl. Acad. Sci. U. S. A., 2003, 100, 3960.
12. (a) F. W. Hobbs, J. Org. Chem., 1989, 54, 3420;
13. (b) T. R. Battersby, D. N. Ang, P. Burgstaller, S. C. Jurczyk, M. T. Bowser, D. D. Buchanan, R. T. Kennedy and S. A. Benner, J. Am. Chem. Soc., 1999, 121, 9781.
14. For purification, the chloride form of AG1-X8 resin must be converted to its bicarbonate form. AG1-X8 (chloride form) is commercially available from Biorad at a cost of $331 USD/500 grams.
15. Amberlite IRA-67 is commercially available from Aldrich Chemical Company, Inc. at a cost of $36 USD/500 grams.
16. Z. Novák, A. Szabó, J. Répási and A. Kotschy, J. Org. Chem., 2003, 68, 3327.
17. For related cross-coupling reactions catalyzed by Pd/C, see: (a) C. P. Mehnert, D. W. Weaver and J. Y. Ying, J. Am, Chem. Soc., 1998, 120, 12289;
18. (b) S. I. Khan and M. W. Grinstaff, J. Org. Chem., 1999, 64, 1077;
19. (c) M. A. De la Rosa, E. Velarde and A. Guzman, Synth. Commun., 1990, 20, 2059;
20. (d) H. Hagiwara, Y. Shimizu, T. Hoshi, T. Suzuki, M. Ando, K. Ohkubo and C. Yokoyama, Tetrahedron Lett., 2001, 42, 4349;
21. (e) L. Djakovitch and K. Koehler, J. Am. Chem. Soc., 2001, 123, 5990;
22. (f) H. Sakurai, T. Tsukuda and T. Hirao, J. Org. Chem., 2002, 67, 2721;
23. (g) C. R. LeBlond, A. T. Andrews, Y. Sun and J. R. Sowa, Org. Lett., 2001, 3, 1555;
24. (h) D. S. Ennis, J. McManus, W. Wood-Kaczmar, J. Richardson, G. E. Smith and A. Carstairs, Org. Process Res. Dev., 1999, 3, 248;
25. (i) K. Köhler, R. G. Heidenreich, J. G. E. Krauter and J. Pietsch, Chem. Eur. J., 2002, 8, 622;
26. (j) G. Zhang, Synlett, 2005, 619.
27. Diagram presented In some cases, furanopyridine by-products (e.g., i) are formed, albeit in minor quantities. Compounds of this type are potent antiviral agents. See: (a) T. S. Mansour, C. A. Evans, M. Charron and B. E. Korba, Bioorg. Med. Chem. Lett., 1997, 7, 303;
28. (b) A. Carangio, C. McGuigan, G. Andrei, R. Snoeck, E. De Clercq and J. Balzarini, Antiviral Chem. Chemother., 2001, 12, 187, see also references therein.
29. G. Giller, T. Tasara, B. Angerer, K. Mühlegger, M. Amacker and H. Winter, Nucleic Acids Res., 2003, 31, 2630.
30. For reviews of the Heck reaction, see: (a) A. B. Dounay and L. E. Overman, Chem. Rev., 2003, 103, 2945;
31. (b) I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009;
32. (c) C. Amatore and A. Jutand, J. Organomet. Chem., 1999, 576, 254.
33. M. Ashwell, A. S. Jones, A. Kumar, J. R. Sayers, R. T. Walker, T. Sakuma and E. De Clercq, Tetrahedron, 1987, 43, 4601.
34. H. Griengl, W. Hayden, W. Schwarz, H. Bachmayer and B. Rosenwirth, Eur. J. Med. Chem., 1985, 20, 105.