Selective palladium-catalyzed aminations on 2-chloro-3-iodo- and 2-chloro-5-iodopyridine

Synlett

Volumn , Issue 12, 2002, Pages 1995-1998

  Maes, Bert U W ^a   Loones, Kristof T J ^a   Jonckers, Tim H M ^a   Lemière, Guy L F ^a   Dommisse, Roger A ^a   Haemers, Achiel ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

Aminations; Chloro iodopyridines; Diarylamines; Iodobenzenes; Palladium

Indexed keywords

2 CHLORO 3 IODOPYRIDINE; 2 CHLORO 5 IODOPYRIDINE; 4 METHYLANILINE; ANILINE DERIVATIVE; CESIUM; IODOBENZENE; PALLADIUM; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYST; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036454157     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35579     Document Type: Article

References (32)

1. (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348.
2. (b) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609.
3. For recent reviews on Pd-catalyzed amination see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
4. For recent reviews on Pd-catalyzed amination see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
5. For recent reviews on Pd-catalyzed amination see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
6. For recent reviews on Pd-catalyzed amination see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
7. (a) Evans, B. E.; Rittle, K. E.; Bock, M. G.; Dipardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J. J. Med. Chem. 1988, 31, 2235.
8. (b) Ariëns, E. J.; Beld, A. J.; Rodrigues de Miranda, J. F.; Simonis, A. M. In The Receptors a Comprehensive Treatise; O'Brien, R. D., Ed.; Plenum Press: New York, 1979.
9. Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Dommisse, R. Tetrahedron 2001, 57, 7027.
10. 2-Chloro-3-iodo- and 2-chloro-5-iodopyridine were prepared from the corresponding commercially available amino derivatives via diazotization and subsequent reaction with KI: Sakamoto, T.: Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1985, 33, 4764.
11. Examples of chemoselective palladium-catalyzed C-C cross-coupling reactions on chloro-iodopyridines: (a) Mello, J. V.; Finney, N. S. Org. Lett. 2001, 3, 4263. (b) Baxter P. N. W.: J. Org. Chem.; 2000, 65: 1257. (c) Muratake, H.: Tonegawa M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400. (d) Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1993, 49, 49. (e) Sakamoto, T.; Kondo, Y.; Watanabe, R.; Yamanaka, H. Chem. Pharm. Bull. 1986, 34, 2719.
12. Examples of chemoselective palladium-catalyzed C-C cross-coupling reactions on chloro-iodopyridines: (a) Mello, J. V.; Finney, N. S. Org. Lett. 2001, 3, 4263. (b) Baxter P. N. W.: J. Org. Chem.; 2000, 65: 1257. (c) Muratake, H.: Tonegawa M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400. (d) Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1993, 49, 49. (e) Sakamoto, T.; Kondo, Y.; Watanabe, R.; Yamanaka, H. Chem. Pharm. Bull. 1986, 34, 2719.
13. Examples of chemoselective palladium-catalyzed C-C cross-coupling reactions on chloro-iodopyridines: (a) Mello, J. V.; Finney, N. S. Org. Lett. 2001, 3, 4263. (b) Baxter P. N. W.: J. Org. Chem.; 2000, 65: 1257. (c) Muratake, H.: Tonegawa M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400. (d) Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1993, 49, 49. (e) Sakamoto, T.; Kondo, Y.; Watanabe, R.; Yamanaka, H. Chem. Pharm. Bull. 1986, 34, 2719.
14. Examples of chemoselective palladium-catalyzed C-C cross-coupling reactions on chloro-iodopyridines: (a) Mello, J. V.; Finney, N. S. Org. Lett. 2001, 3, 4263. (b) Baxter P. N. W.: J. Org. Chem.; 2000, 65: 1257. (c) Muratake, H.: Tonegawa M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400. (d) Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1993, 49, 49. (e) Sakamoto, T.; Kondo, Y.; Watanabe, R.; Yamanaka, H. Chem. Pharm. Bull. 1986, 34, 2719.
15. Examples of chemoselective palladium-catalyzed C-C cross-coupling reactions on chloro-iodopyridines: (a) Mello, J. V.; Finney, N. S. Org. Lett. 2001, 3, 4263. (b) Baxter P. N. W.: J. Org. Chem.; 2000, 65: 1257. (c) Muratake, H.: Tonegawa M.; Natsume, M. Chem. Pharm. Bull. 1998, 46, 400. (d) Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1993, 49, 49. (e) Sakamoto, T.; Kondo, Y.; Watanabe, R.; Yamanaka, H. Chem. Pharm. Bull. 1986, 34, 2719.
16. 16 These conditions do not allow a large functional group compatibility on both coupling partners: Parrot, I.; Ritter, G.; Wermuth, C. G.; Hibert, M. Synlett 2002, 1123.
17. 3 as base see: Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144.
18. Wolfe, J. P.; Tomori H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
19. Ali, M. H.; Buchwald, S. L. J. Org. Chem. 2001, 66, 2560.
20. Košmrlj, J.; Maes, B. U. W.; Lemière, G. L. F.; Haemers, A. Synlett 2000, 1581.
21. 3 (8 hours).
22. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066.
23. For the palladium-catalyzed N-arylation of sulfoximines, the use of aryl iodides with Pd-BINAP as catalyst in combination with a mild carbonate base has been reported. To ensure product formation in acceptable yields the use of additives (LiBr, LiCl, AgOTf) was essential: Bolm, C.; Hildebrand, J. P. J. Org. Chem. 2000, 65, 169.
24. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
25. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
26. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
27. Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307.
28. Buchwald originally used a double amount of XANTPHOS (Pd/2L instead of Pd/L)
29. 2 (200 mL). The filtrate was evaporated and the resulting crude product was purified by flash column chromatography.
30. 2 (200 mL). The filtrate was evaporated and the resulting crude product was purified by flash column chromatography.
31. 3): 141.5, 140.1, 138.7, 138.3, 132.8, 130.2, 125.7, 124.2, 119.9, 20.7.
32. 2 (200 mL). The filtrate was evaporated and the resulting crude product was purified by flash column chromatography. The characterization data of N-(3-carbethoxyphenyl)-N-methylaniline, N-(4-carbethoxyphenyl)-N-methylaniline and 3-cyano-2′-carbethoxydiphenylamine were identical with those