Palladium-catalyzed cross-coupling reactions of dry arenediazonium o-benzenedisulfonimides with aryltin compounds

Synthesis

Volumn , Issue 7, 2006, Pages 1117-1122

  Dughera, Stefano ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

Cross coupling; Diazonium compounds; Palladium; Stille reaction; Sulfur

Indexed keywords

CATALYST ACTIVITY; PALLADIUM; SULFUR;

ARYLTIN DERIVATIVES; CROSS-COUPLING; DIAZONIUM COMPOUNDS; STILLE REACTIONS;

AROMATIC COMPOUNDS;

BENZENEDISULFONIMIDE DERIVATIVE; BENZENESULFONAMIDE DERIVATIVE; DIAZONIUM COMPOUND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TIN DERIVATIVE; TRIBUTYLTIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SYNTHESIS;

EID: 33645989196     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926373     Document Type: Article

References (61)

1. Reviews: (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
2. (b) Geissler, H. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998, Chap. 2.10, 158-183.
3. (c) Tsuji, J. Transition Metal Reagents and Catalysts; Wiley: Chichester U.K., 2000, Chap. 3, 27-108.
4. Reviews (a) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167.
5. (b) Kalinin, V. N. Synthesis 1992, 413.
6. (c) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
7. (d) Snieckus, V. Chem. Rev. 1990, 90, 879.
8. (e) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester U.K., 2004, Chap. 3, 288-348; and references therein.
9. Reviews: (a) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
10. (b) Stanforth, S. Tetrahedron 1998, 54, 263.
11. (a) Gomberg, M.; Bachmann, W. E. J. Am. Chem. Soc. 1924, 46, 2339.
12. (b) Heilbron, I. M.; Hey, D. H.; Cambrest, A. J. Chem. Soc. 1940, 1279.
13. (c) Beadle, J. R.; Korzeniowski, S. H.; Rosenberg, D. E.; Garcia-Slenga, B. J.; Gokel, G. W. J. Org. Chem. 1984, 49, 1594.
14. (d) Korzeniowski, S. H.; Blum, L.; Gokel, G. W. Tetrahedron Lett. 1977, 22, 1871.
15. Reviews: (a) Tamao, K.; Kumada, M. In The Chemistry of the Metal-Carbon Bond, Vol. 4; Hartley, F. R., Ed.; Wiley: New York, 1987, 820.
16. (b) Sekiya, A.; Ishikawa, N. J. Organomet. Chem. 1976, 118, 349.
17. (c) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
18. (d) Erdik, E. Tetrahedron 1992, 48, 9577.
19. (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 513.
20. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
21. (c) Martin, A. R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221.
22. (a) Millstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636.
23. (b) Millstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981.
24. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
25. (d) Mitchell, T. N. Synthesis 1992, 803.
26. (e) Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523.
27. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. (N.Y.) 1997, 50, 1.
28. (g) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
29. Ritter, K. Synthesis 1993, 735.
30. (a) Darses, S.; Tuyet, J.; Genet, J.-P. Tetrahedron Lett. 1996, 37, 3857.
31. (b) Darses, S.; Tuyet, J.; Brayer, J.-L.; Demoute, J.-P.; Genet, J.-P. Bull. Soc. Chim. Fr. 1996, 133, 1095.
32. (c) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405.
33. (d) Sengupta, S.; Sadhukhan, S. K. Tetrahedron Lett. 1998, 39, 715.
34. (a) Kikukawa, K.; Kono, K.; Wada, F.; Matsuda, T. Chem. Lett. 1982, 35.
35. (b) Kikukawa, K.; Umekawa, H.; Matsuda, T. J. Organomet. Chem. 1986, 311, C44.
36. (c) Kikukawa, K.; Idemoto, T.; Katayama, A.; Kono, K.; Wada, F.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1987, 1511.
37. (d) Neumann, W. P.; Wicenec, C. Chem. Ber. 1991, 124, 2297;
38. (e) Kang, S.-K.; Kim, J.-S.; Choi, S.-C.; Lim, K.-H. Synthesis 1998, 1249.
39. (a) Kikukawa, K.; Kono, K.; Wada, F.; Matsuda, T. J. Org. Chem. 1983, 48, 1333; and references therein.
40. (b) Bumagin, N. A.; Sukhomlinova, L. I.; Tolstaya, T. P.; Beletskaya, I. P. Russ. J. Org. Chem. 1994, 30, 1605.
41. Barbero, M.; Degani, I.; Dughera, S.; Fochi, R. Synthesis 2004, 2386; and references therein.
42. Sherwood, J. R.; Short, W. F.; Stansfield, R. J. Chem. Soc. 1932, 1832.
43. Nunez, A.; Sanchez, A.; Burgos, C.; Alvarez-Builla, J. Tetrahedron 2004, 60, 6217.
44. De Luca, G.; Renzi, G.; Cipollini, R.; Pizzabiocca, A. J. Chem. Soc., Perkin Trans. 1 1980, 1901.
45. Klement, I.; Rottlaender, M.; Tucker, C. E.; Majid, T. N.; Knochel, P.; Venegas, P.; Cahiez, G. Tetrahedron 1996, 52, 7201.
46. Bjorklund, C.; Nilsson, M. Acta Chem. Scand. 1968, 22, 2338.
47. Effenberger, F.; Koch, M.; Streicher, W. Chem. Ber. 1991, 124, 163.
48. Idoux, J. P.; Cantwell, V. S.; Nelson, S. O.; Hollier, P.; Zarrillo, R. J. Org. Chem. 1974, 39, 3946.
49. Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302.
50. Beaven, G. H.; Johnson, E. A. Spectrochim. Acta 1959, 14, 67.
51. Nakamura, M.; Sawasaki, K.; Okamoto, Y.; Takamuku, S. J. Chem. Soc., Perkin Trans. 1 1994, 141.
52. Clennan, E. L.; Mehrsheik-Mohammadi, M. E. Magn. Reson. Chem. 1985, 23, 985.
53. Pelter, A.; Rowland, M.; Clements, G. Synthesis 1987, 51.
54. Xia, M.; Chen, Z.-C. Synth. Commun. 1999, 29, 2457.
55. Ohta, A.; Akita, Y.; Ohkuwa, T.; Chiba, M.; Fukunaga, R. Heterocycles 1990, 31, 1951.
56. Kolodziuk, R.; Penciu, A.; Tollabi, M.; Framery, E.; Goux-Henry, C.; Iourtchenko, A.; Sinou, D. J. Organomet. Chem. 2003, 384.
57. Kozyrod, R. P.; Morgan, J.; Pinhey, J. T. Aust. J. Chem. 1985, 38, 1147.
58. Outten, R. A.; Daves, G. D. J. Org. Chem. 1989, 54, 29.
59. Clarke, P. I.; Howie, R. A.; Wardell, J. L. J. Inorg. Nucl. Chem. 1974, 36, 2449.
60. Azizian, H.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 215, 49.
61. Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 1713