2-(Azidomethyl)phenylboronic acid in the synthesis of isoquinoline derivatives

Russian Chemical Bulletin

Volumn 54, Issue 7, 2005, Pages 1606-1611

  Ganina, O G ^a,b   Zamotaeva, S G ^a   Nosarev, M A ^a   Kosenkova, O V ^a   Naumov, M I ^a   Shavyrin, A S ^c   Finet, J P ^d   Fedorov, A Yu ^a  

^a LOBACHEVSKY STATE UNIVERSITY OF NIZHNY NOVGOROD   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c G A RAZUVAEV INSTITUTE OF ORGANOMETALLIC CHEMISTRY   (Russian Federation)

^d AIX MARSEILLE UNIVERSITY   (France)

Author keywords

arylation; 2 (azidomethyl)phenylboronic acid; Isochromanes; Isoquinolines; Lead tetraacetate; Organolead compounds; Reductive coupling

Indexed keywords

EID: 31344472005     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-006-0011-y     Document Type: Article

References (41)

1. F. Ullmann, Ber., 1903, 36, 2389;
2. F. Ullmann, Ber., 1904, 37, 853;
3. I. Goldberg, Ber., 1906, 39, 1691.
4. (a) R. J. Lewis, Sax's Dangerous Properties of Industrial Materials, Van Nostrand Reinhold, New York, 1992, 4296 pp.;
5. (b) R. E. Lenga, The Sigma-Aldrich Library of Chemical Safety, Sigma-Aldrich, Milwaukee, 1988, 5000 pp.
6. (a) S. V. Ley and A. W. Thomas, Angew. Chem., Int. Ed. Engl., 2003, 42, 5400;
7. (b) J.-P. Finet, A. Yu. Fedorov, S. Combes, and G. Boyer, Curr. Org. Chem., 2002, 6, 597.
8. (a) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457;
9. (b) A. Suzuki, J. Organomet. Chem., 1999, 576, 147;
10. (c) P. Lloyd-Williams and E. Giralt, Chem. Soc. Rev., 2001, 30, 145;
11. (d) J. Hassan, M. Sevignon, C. Gozzi, E. Schultz, and M. Lemaire, Chem. Rev., 2002, 102, 1359;
12. (e) S. D. Walker, T. E. Barder, J. R. Martinelli, and S. L. Buchwald, Angew. Chem., Int. Ed. Engl., 2004, 43, 1871;
13. (f) M. Miura, Angew. Chem., Int. Ed. Engl., 2004, 43, 2201.
14. (a) V. V. Rostovtsev, L. G. Green, V. V. Fokin, and K. B. Sharpless, Angew. Chem., Int. Ed., 2002, 41, 2596;
15. (b) E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 298.
16. A. Yu. Fedorov, A. A. Shchepalov, A. V. Bol'shakov, A. S. Shavyrin, Yu. A. Kurskii, J.-P. Finet, and S. V. Zelentsov, Izv. Akad. Nauk, Ser. Khim., 2004, 356
17. [Russ. Chem. Bull., Int. Ed., 2004, 53, 370].
18. (a) M. Chrzanowska and M. D. Rozwadowska, Chem. Rev., 2004, 104, 3341;
19. (b) D. J. Milanowski, K. R. Gustafson, J. A. Kelly, and J. B. McMahon, J. Nat. Prod., 2004, 67, 70;
20. (c) A. Bermejio, I. Andreu, F. Suvire, S. Leonce, D. H. Caignard, P. Renard, A. Pierre, R. D. Enriz, D. Cortes, and N. Cabedo, J. Med. Chem., 2002, 45, 5058;
21. (d) M. Cushman, M. Jayaraman, J. A. Vroman, A. K. Fukunaga, B. M. Fox, G. Kohlhagen, D. Strumberg, and Y. Pommier, J. Med. Chem., 2000, 43, 3688;
22. (e) J. E. van Muijlwijk-Koezen, H. Timmerman, H. van der Goot, W. M. P. B. Menge, J. F. von D. Künzel, M. de Groote, and A. P. Ijzerman, J. Med. Chem., 2000, 43, 2227.
23. D. A. Culkin and J. F. Hartwig, Acc. Chem. Res., 2003, 36, 234;
24. W. A. Herrmann, Angew. Chem., Int. Ed., 2002, 41, 1290;
25. M. Miura and M. Nomura, Top. Curr. Chem., 2002, 219, 211.
26. J. T. Pinhey, in Comprehensive Organometallic Chemistry II, Eds E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon Press, Oxford, 1995, Vol. 11, pp. 461-485.
27. (a) A. Yu. Fedorov, F. Carrara, and J.-P. Finet, Tetrahedron Lett., 2001, 42, 5875;
28. (b) M. I. Naumov, O. G. Ganina, A. S. Shavirin, I. P. Beletskaya, J.-P. Finet, and A. Yu. Fedorov, Synthesis, 2005, 1178.
29. J. Morgan and J. T. Pinhey, J. Chem. Soc., Perkin Trans. 1, 1990, 715.
30. J.-P. Finet, Ligand Coupling Reactions with Heteroatomic Compounds, Pergamon Press, Oxford, 1998, 291 pp.
31. C. I. Elliott and J. P. Konopelski, Tetrahedron, 2001, 57, 5683.
32. Organobismuth Chemistry, Eds H. Suzuki and Y. Matano, Elsevier, Amsterdam, 2001, 619 pp.
33. V. V. Grushin, Chem. Soc. Rev., 2000, 29, 315.
34. A. Yu. Fedorov and J.-P. Finet, Eur. J. Org. Chem., 2004, 2040 and references therein.
35. (a) G. H. Jones, J. B. D. Mackenzie, A. Robertson, and W. B. Whalley, J. Chem. Soc., 1949, 562;
36. (b) D. H. R. Barton, D. M. X. Donnelly, J.-P. Finet, and P. J. Guiry, J. Chem. Soc., Perkin Trans. 1, 1992, 1365;
37. (c) S. Combes, J.-P. Finet, and D. Siri, J. Chem. Soc., Perkin Trans. 1, 2002, 38.
38. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997, 320 pp.
39. G. L'Abbe, Chem. Rev., 1969, 69, 345;
40. I. Foch, L. Parkanyi, G. Besenyei, L. I. Simandi, and A. Kalman, J. Chem. Soc., Dalton Trans., 1999, 293.
41. J. K. M. Sanders and B. K. Hunter, Modern NMR Spectroscopy. A Guide for Chemists, Oxford University Press, New York, 1997, 314 pp.