Addition reactions of E-E and E-H bonds to triple bond of alkynes catalyzed by Pd, Pt, and Ni complexes (E=S, Se)

Pure and Applied Chemistry

Volumn 79, Issue 6, 2007, Pages 1041-1056

  Beletskaya, Irina P ^a   Ananikov, Valentine P ^b  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Addition reactions; Green chemistry; Selenium species; Sulfur species; Transition metal catalysis

Indexed keywords

EID: 34250660100     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200779061041     Document Type: Conference Paper

References (46)

1. A. Togni, H. Grützmacher (Eds.). Catalytic Heterofunctionalization, Wiley-VCH, Weinheim (2001).
2. (a) I. Beletskaya, C. Moberg. Chem. Rev. 99, 3435 (1999);
3. (b) T. Kondo, T. Mitsudo. Chem. Rev. 100, 3205 (2000);
4. (c) I. Beletskaya, C. Moberg. Chem. Rev. 106, 2320 (2006).
5. (a) M. Beller, J. Seayad, A. Tillack, H. Jiao. Angew. Chem., Int. Ed. 43, 3368 (2004);
6. (b) F. Alonso, I. P. Beletskaya, M. Yus. Chem. Rev. 104, 3079 (2004).
7. (a) A. Ogawa. J. Organomet. Chem. 611, 463 (2000);
8. (b) L.-B. Han, C. Zhang, H. Yazawa, S. Shimada. J. Am. Chem. Soc. 126, 5080 (2004).
9. (a) T. G. Back, M. V. Krishna. J. Org. Chem. 53, 2533 (1988);
10. (b) A. Ogawa, H. Yokoyama, K. Yokoyama, T. Masawaki, N. Kambe, N. Sonoda. J. Org. Chem. 56, 5721 (1991).
11. (a) A. K. Kondoh, K. Takami, H. Yorimitsu, K. Oshima. J. Org. Chem. 70, 6468 (2005);
12. (b) B. A. Trofimov. Curr. Org. Chem. 6, 1121 (2002);
13. (c) L. Benati, L. Capella, P. C. Montevecchi, P. Spagnolo. J. Chem. Soc., Perkin Trans. 1035 (1995);
14. (d) Y. Ichinose, K. Wakamatsu, K. Nozaki, J.-L. Birbaum, K. Oshima, K. Utimoto. Chem. Lett. 1647 (1987);
15. (e) B. A. Trofimov. Russ. Chem. Rev. 50, 138 (1981);
16. (f) W. E. Truce, G. J. W. Tichenor. J. Org. Chem. 37, 2391 (1972);
17. (g) W. E. Truce, R. F. Heine. J. Am. Chem. Soc. 79, 5311 (1957).
18. H. Kuniyasu, A. Ogawa, S. Miyazaki, I. Ryu, N. Kambe, N. Sonoda. J. Am. Chem. Soc. 113, 9796 (1991).
19. V. P. Ananikov, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko. Organometallics 22, 1414 (2003).
20. V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko. J. Organomet. Chem. 687, 451 (2003).
21. (a) V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya. Dokl. Chem. 390, 112 (2003);
22. (b) V. P. Ananikov, I. P. Beletskaya. Dokl. Chem. 389, 81 (2003).
23. V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya, V. N. Khrustalev, M. Yu. Antipin. Organometallics 24, 1275 (2005).
24. (a) R. Oilunkaniemi, R. S. Laitinen, M. Ahlgren. J. Organomet. Chem. 587, 200 (1999);
25. (b) R. Oilunkaniemi, R. S. Laitinen, M. Ahlgren. J. Organomet. Chem. 623, 168 (2001);
26. (c) R. Zanella, R. Ros, M. Graziani. Inorg. Chem. 12, 2736 (1973);
27. (d) I. Nakanishi, S. Tanaka, K. Matsumoto, S. Ooi. Acta Crystallogr., Sect. C 50, 58 (1994).
28. S. Dey, V. K. Jain, B. Varghese. J. Organomet. Chem. 623, 48 (2001).
29. (a) V. K. Jain, S. Kannan, E. R. T. Tiekink. J. Chem. Res. (M) 0501 (1994);
30. (b) M. S. Hannu, R. Oilunkaniemi, R. S. Laitinen, M. Ahlgen. Inorg. Chem. Commun. 3, 397 (2000).
31. V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya. Synlett 1015 (2005).
32. (a) V. P. Ananikov, I. P. Beletskaya. Org. Biomol. Chem. 2, 284 (2004);
33. (b) V. P. Ananikov, I. P. Beletskaya. Russ. Chem. Bull. 53, 561 (2004).
34. (a) A. Ogawa, T. Ikeda, K. Kimura, T. Hirao. J. Am. Chem. Soc. 121, 5108 (1999);
35. (b) H. Kuniyasu, A. Ogawa, K. Sato, I. Ryu, N. Kambe, N. Sonoda. J. Am. Chem. Soc. 114, 5902 (1992).
36. (a) H. Kuniyasu, A. Ogawa, K.-I. Sato, I. Ryu, N. Sonoda. Tetrahedron Lett. 38, 5525 (1992);
37. (b) I. Kamiya, E. Nishinaka, A. Ogawa. J. Org. Chem. 70, 696 (2005).
38. (a) V. P. Ananikov, D. A. Malyshev, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko. J. Organomet. Chem. 679, 162 (2003);
39. (b) V. P. Ananikov, D. A. Malyshev, I. P. Beletskaya. Russ. J. Org. Chem. 38, 1528 (2002).
40. V. P. Ananikov, D. A. Malyshev, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko. Adv. Synth. Catal. 347, 1993 (2005).
41. V. P. Ananikov, I. P. Beletskaya. Russ. Chem. Bull. 52, 811 (2003).
42. (a) M. O. Shulyupin, M. A. Kazankova, I. P. Beletskaya. Org. Lett. 4, 761 (2002);
43. (b) M. A. Kazankova, M. O. Shulyupin, I. P. Beletskaya. Synlett 14, 2155 (2003).
44. V. P. Ananikov, N. V. Orlov, I. P. Beletskaya. Organometallics 25, 1970 (2006).
45. V. P. Ananikov, N. V. Orlov, I. P. Beletskaya. Organometallics 26, 740 (2007).
46. D. A. Malyshev, N. M. Scott, N. Marion, E. D. Stevens, V. P. Ananikov, I. P. Beletskaya, S. P. Nolan. Organometallics 25, 4462 (2006).