Study of a new rate increasing "base effect" in the palladium-catalyzed amination of aryl iodides

Journal of Organic Chemistry

Volumn 69, Issue 18, 2004, Pages 6010-6017

  Meyers, Caroline ^a   Maes, Bert U W ^a   Loones, Kristof T J ^a   Bal, Gunther ^a   Lemière, Guy L F ^a   Dommisse, Roger A ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL IODIDES; CATALYTIC CYCLES; INTERPHASE DEPROTONATION; REACTION RATES;

AMINATION; CARBONATES; CATALYSIS; CATALYSTS; PALLADIUM; RATE CONSTANTS;

IODINE COMPOUNDS;

AMINE; CARBONIC ACID DERIVATIVE; CESIUM; IODIDE; METAL COMPLEX; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMINATION; ARTICLE; BUCHWALD HARTWIG AMINATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; PARTICLE SIZE;

EID: 4344665807     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049774e     Document Type: Article

References (47)

1. (a) Buckingham, J. Dictionary of Natural Products; University Press: Cambridge, MA, 1994.
2. (b) Czarnik, A. W. Acc. Chem. Res. 1996, 29, 112.
3. (c) Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances, 3rd ed.; Thieme: Stuttgart, Germany, 1999.
4. (d) CRC Handbook of Pesticides; Milne, G. W. A., Ed.; CRC Press: Boca Raton, FL, 1994.
5. (e) Waring, D. R.; Hallas, G. The Chemistry and Application of Dyes; Plenum: New York, 1990.
6. (f) Polymers for Lightwave and Integrated Optics; Hornak, L. A., Ed.; Marcel Dekker: New York, 1992.
7. (g) D'Aprano, G.; Leclerc, M.; Zotti, G.; Schiavon, G. Chem. Mater. 1995, 7, 33.
8. (h) Skotheim, T. A.; Elsenbaumer, R. L.; Reynolds, J. R. Handbook of Conducting Polymers, 2nd ed.; Marcel Dekker: New York, 1997.
9. (a) Belfield, A. J.; Brown, G. R.; Foubister, A. J. Tetrahedron 1999, 55, 11399.
10. (b) Lindley, J. Tetrahedron 1984, 40, 1433.
11. (c) Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502.
12. (d) March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992.
13. (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348.
14. (b) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609.
15. For reviews and accounts on the Buchwald-Hartwig reaction see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
16. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
17. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615.
18. (d) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
19. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
20. (f) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
21. (g) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
22. (h) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
23. For a review partly dealing with palladium-catalyzed aminations of aryl chlorides see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
24. Ali, M. H.; Buchwald, S. L. J. Org. Chem. 2001, 66, 2560.
25. Urgaonkar, S.; Xu, J. H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416.
26. 3 has been reported. However, to ensure product formation in acceptable yields the use of additives (LiBr, AgOTf) was essential: Bolm, C.; Hildebrand, J. P. J. Org. Chem. 2000, 65, 169.
27. 3 has been reported. However, to ensure product formation in acceptable yields the use of additives (LiBr, AgOTf) was essential: Bolm, C.; Hildebrand, J. P. J. Org. Chem. 2000, 65, 169.
28. For the Pd-catalyzed amination of aryl iodides with strong MOtBu base see: (a) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
29. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
30. (c) See ref 8.
31. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
32. (e) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
33. (f) Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307.
34. (g) See ref 6.
35. (h) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. J. Org. Chem. 2003, 68, 452.
36. For a preliminary communication see: Maes, B. U. W.; Loones, K. T. J.; Jonckers, T. H. M.; Lemière, G. L. F.; Dommisse, R. A.; Haemers, A. Synlett 2002, 1995.
37. For the Pd-catalyzed amination of azaheteroaryl iodides with strong MOtBu base see: (a) Cheng, J.; Trudell, M. L. Org. Lett. 2001, 3, 1371. Interestingly, a completely opposite regioselectivity has been observed by Cheng and Trudell when they studied the coupling of 2-chloro-5-iodopyridine with 7-azabicyclo[2.2.1]heptane using a Pd-carbene complex.
38. (b) Parrot, I.; Ritter, G.; Wermuth, C. G. G.; Hibert, M. Synlett 2002, 1123.
39. 3 accelerated the amination of azaheteroaryl chloride substrates with anilines: (a) Chloropyridazin-3(2H)-ones: Košmrlj, J.; Maes, B. U. W.; Lemière, G. L. F.; Haemers, A. Synlett 2000, 1581.
40. (b) Dichloropyridines: Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Dommisse, R. Tetrahedron 2001, 57, 7027.
41. 3 (3 equiv) accelerated the amination of aryl bromide substrates with carbazole, indole, and pyrrole: Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 41, 481.
42. 3 (1.4 equiv) as base see: (a) Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6359.
43. 3 used was standardly ground prior to its use. The authors gave no specific reason for this grinding and no effect on the reaction rate was reported. The supplier and quality of the base were not specified.
44. 2/2-(di-tert- butylphosphanyl)biphenyl (DTBPB) as precatalyst for the amination of aryl chlorides in toluene: Zim, D.; Buchwald, S. L. Org. Lett. 2003, 5, 2413.
45. 2/2-(di-tert- butylphosphanyl)biphenyl (DTBPB) as precatalyst for the amination of aryl chlorides in toluene: Zim, D.; Buchwald, S. L. Org. Lett. 2003, 5, 2413.
46. 2 were unsuccessful since the contact surface area was too small: Rouquerol, F.; Rouquerol, J.; Sing, K. Adsorption by powders & porous solids; Academic Press: London, UK, 1999. Consequently, only the difference in particle shape and size of the cesium carbonate particles, observed by recording SEM images, could be taken into account.
47. 3 of Acros (99.5%) ("type 1") gave 84% isolated yield of 2-chloro-3-(morpholin-4-yl)pyridine in a reaction time of 17 h.