Palladium-catalyzed cross-coupling alkylation of arenediazonium o-benzenedisulfonimides

Synthesis

Volumn , Issue 3, 2008, Pages 0474-0478

  Barbero, Margherita ^a   Cadamuro, Silvano ^a   Dughera, Stefano ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

Cross coupling; Diazo compounds; Palladium; Stille reaction; Suzuki reaction

Indexed keywords

BENZENEDISULFONIMIDE; PRECATALYSTS;

ALKYLATION; CATALYSIS; DERIVATIVES; METHYLATION; REACTION KINETICS;

PALLADIUM COMPOUNDS;

2 METHYL 4 NITROBENZENEDIAZONIUM 2 BENZENEDISULFONIMIDE; 3 CHLORO 4 METHOXYBENZENEDIAZONIUM 2 BENZENEDISULFONIMIDE; ARENEDIAZONIUM 2 BENZENEDISULFONIMIDE DERIVATIVE; DIAZONIUM COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CROSS COUPLING REACTION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STILLE REACTION; SUZUKI REACTION; THIN LAYER CHROMATOGRAPHY;

EID: 39349090661     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032027     Document Type: Article

References (33)

1. (a) Artuso, E.; Barbero, M.; Degani, I.; Dughera, S.; Fochi, R. Tetrahedron 2006, 62, 3146.
2. (b) Barbero, M.; Cadamuro, S.; Dughera, S. Synthesis 2006, 3443.
3. (c) Barbero, M.; Cadamuro, S.; Dughera, S.; Giaveno, C. Eur. J. Org. Chem. 2006, 4884.
4. Millstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636.
5. Dughera, S. Synthesis 2006, 1117.
6. (a) Darses, S.; Tuyet, J.; Genet, J.-P. Tetrahedron Lett. 1996, 37, 3857.
7. (b) Darses, S.; Tuyet, J.; Brayer, J.-L.; Demoute, J.-P.; Genet, J.-P. Bull. Soc. Chim. Fr. 1996, 133, 1095.
8. (c) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405.
9. (d) Sengupta, S.; Sadhukhan, S. K. Tetrahedron Lett. 1998, 39, 715.
10. (e) Kikukawa, K.; Kono, K.; Wada, F.; Matsuda, T. Chem. Lett. 1982, 35.
11. (f) Kikukawa, K.; Umekawa, H.; MatsudaT, J. Organomet. Chem. 1986, 311, C44.
12. (g) Kikukawa, K.; Idemoto, T.; Katayama, A.; Kono, K.; Wada, F.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1987, 1511.
13. (h) Neumann, W. P.; Wicenec, C. Chem. Ber. 1991, 124, 2297.
14. (i) Kang, S.-K.; Kim, J.-S.; Choi, S.-C.; Lim, K.-H. Synthesis 1998, 1249.
15. (a) Kikukawa, K.; Kono, K.; Wada, F.; Matsuda, T. J. Org. Chem. 1983, 48, 1333.
16. (b) Bumagin, N. A.; Sukhomlinova, L. I.; Tolstaya, T. P.; Beletskaya, I. P. Russ. J. Org. Chem. 1994, 30, 1605.
17. (c) Andrus, M. B.; Song, C. Org. Lett. 2001, 3, 3761.
18. Barbero, M.; Degani, I.; Dughera, S.; Fochi, R. Synthesis 2004, 2386; and references therein.
19. Schmidt, A. W.; Schoeller, V. Chem. Ber. 1941, 258.
20. Broxton, T. J.; Cameron, D. G.; Topsom, R. D. J. Chem. Soc., Perkin Trans. 2 1974, 256.
21. Reilly, J.; Hickinbottom, W. J. J. Chem. Soc. 1920, 103.
22. Read, R. R.; Mullin, D. B. J. Am. Chem. Soc. 1928, 50, 1763.
23. Jenneskens, L. W.; De Wolf, W. H.; Bickelhaupt, F. Synthesis 1985, 647.
24. Birch, S. F.; Dean, R. A.; Fidler, F. A.; Lowry, R. A. J. Am. Chem. Soc. 1949, 71, 1362.
25. Fischer, A.; Henderson, G. N.; RayMahasay, S. Can. J. Chem. 1987, 65, 1233.
26. Griffin, G. W.; Manmade, A. J. Org. Chem. 1972, 37, 2589.
27. Suzuki, A. J. Organomet. Chem. 2002, 653, 83.
28. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; Wiley: Chichester U.K., 2004, Chap. 1, 1-24 and Chap. 3, 288-348 and references therein.
29. Card, R. J.; Trahanovsky, W. S. J. Org. Chem. 1980, 45, 2560.
30. Morgan, G. T.; Hickinbottom, W. J. J. Chem. Soc. 1921, 1879.
31. Brown, H. C.; Bonner, W. H. J. Am. Chem. Soc. 1954, 76, 605.
32. Huang, R. L.; Lee, H. H. J. Chem. Soc. C 1966, 929.
33. Barbero, M.; Crisma, M.; Degani, I.; Fochi, R.; Perracino, P. Synthesis 1998, 1171.