Reductive dimerization of 2- and 6-iodopurines: Side reaction in Pd-catalyzed cross-coupling of iodopurines

Collection of Czechoslovak Chemical Communications

Volumn 72, Issue 10, 2007, Pages 1365-1374

  Tobrman, Tomáš ^a   Dvořák, Dalimil ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Biaryls; Cross coupling reactions; Nucleosides; Pd catalysis; Purines; Reductive dimerization

Indexed keywords

EID: 38749104638     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20071365     Document Type: Article

References (26)

1. a) Hocek M., Votruba I., Dvořáková H.: Tetrahedron 2003, 59, 607, and references therein;
2. b) Brathe A., Gundersen L.-L., Nissen-Meyer J., Rise F., Spilsberg B.: Bioorg. Med. Chem. Lett. 2003, 13, 877;
3. c) Yao S.-W., Lopes V. H. C., Fernández F., García-Mera X., Morales M., Rodríguez-Borges J. E., Cordeiro M. N. D. S.: Bioorg. Med. Chem. 2003, 11, 4999;
4. d) Fernández F., García-Mera X., Morales M., Vilarino L., Caamano O., De Clercq E.: Tetrahedron 2004, 60, 9245;
5. e) Bakkestuen A. K., Gundersen L.-L., Utenova B. T.: J. Med. Chem. 2005, 48, 2710;
6. f) Fernández F., García-Mera X., Morales M., Rodríguez-Borges J. E., De Clercq E.: Synthesis 2002, 1084.
7. For review, see: Hocek M.: Eur. J. Org. Chem. 2003, 245.
8. a) Havelková M., Hocek M., Česnek M., Dvořák D.: Synlett 1999, 1145;
9. b) Havelková M., Hocek M., Dvořák D.: Synthesis 2001, 1704;
10. c) Hocek M., Holý A., Votruba I., Dvořáková H.: J. Med. Chem. 2000, 43, 1817;
11. d) Hocek M., Holý A., Votruba I., Dvořáková H.: Collect. Czech. Chem. Commun. 2000, 65, 1683.
12. Selected examples: a) Gundersen L.-L., Bakkestuen A. K., Aasen A. J., Overas H., Rise F.: Tetrahedron 1994, 50, 9743;
13. b) Gundersen L.-L.: Tetrahedron Lett. 1994, 35, 3155;
14. c) Fujiwara T., Kimoto M., Sugiyama H., Yokoyama S.: Bioorg. Med. Chem. Lett. 2001, 11, 2221;
15. d) Gundersen L.-L., Nissen-Meyer J., Spilsberg D.: J. Med. Chem. 2002, 45, 1383;
16. e) Hocek M., Holý A., Votruba I., Dvoř́ková H.: Collect. Czech. Chem. Commun. 2001, 66, 483.
17. For examples see: a) Volpini R., Constanzi S., Lambertucci C., Taffi S., Vittori S., Klotz K.-N., Cristalli G.: J. Med. Chem. 2002, 45, 3271;
18. b) Tanji K.-I., Higashino T.: Chem. Pharm. Bull. 1988, 36, 1935;
19. c) Sessler J. L., Sathiosatham M., Brown C. T., Rhodes T. A., Wiederrecht G.: J. Am. Chem. Soc. 2001, 123, 3655.
20. Lakshman K. M., Gunda P., Pradhan P.: J. Org. Chem. 2005, 70, 10329.
21. a) Duker N. J., Sperling J., Soprano K. J., Druin D. P., Davis A., Ashworth R.: J. Cell. Biochem. 2001, 81, 393, and references therein;
22. b) Čerňa I., Pohl R., Klepetářová B., Hocek M.: Org. Lett. 2006, 8, 5389.
23. Guthmann H., Könemann M., Bach T.: Eur. J. Org. Chem. 2007, 632.
24. Dörwald F. Z.: Side Reactions in Organic Synthesis: A Guide to Successful Synthesis Design, p. 287. Wiley-VCH, Weinheim 2004.
25. Nair V., Richardson S. G.: J. Org. Chem. 1980, 45, 3969.
26. Legraverend M., Ludwig O., Bisagni E., Leclerc S., Meijer L., Giocanti N., Sadri R., Favaudon V.: Bioorg. Med. Chem. 1999, 7, 1281.