Microwave-assisted Pd(0)-catalyzed amination of aryl halides on solid support

Molecular Diversity

Volumn 7, Issue 2-4, 2003, Pages 181-184

  Weigand, Klaus ^a   Pelka, Sylvie ^a  

^a NOVARTIS RESEARCH INSTITUTE   (Austria)

Author keywords

Aryl amination; Microwave; Pd(0) catalysis; Rink resin; Solid phase chemistry

Indexed keywords

HALIDE; PALLADIUM; RESIN;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CLINICAL PROTOCOL; HEATING; MICROWAVE COOKING; MICROWAVE RADIATION; PRIORITY JOURNAL; REACTION TIME;

CARBON; CATALYSIS; CHEMISTRY, ORGANIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HEAT; MICROWAVES; MODELS, CHEMICAL; PALLADIUM; TEMPERATURE; TIME FACTORS;

EID: 0345825856     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006821.42063.6b     Document Type: Article

References (17)

1. For recent reviews, see: (a) Larhed, M., Moberg, C. and Hallberg, A., Microwave-accelerated homogeneous catalysis in organic chemistry, Acc. Chem. Res., 35 (2002) 717-727.
2. (b) Olofson, K., Hallberg, A. and Larhed, M., Transition Metal Catalysis and Microwave Flash Heating in Organic Chemistry, in Loupy, A. (ed.), Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, 2002, pp 379-404.
3. (a) Larhed, M., Lindeberg, G. and Hallberg, A., Rapid microwave-assisted Suzuki coupling on solid phase, Tetrahedron Lett., 37 (1996) 8219-8222.
4. (b) Alterman, M. and Halberg, A., Fast microwave-assisted preparation of aryl and vinyl halides and the corresponding tetrazoles from organo-halides, J. Org. Chem., 65 (2000) 7984-7989.
5. (c) Combs, A. P., Saubern, S., Rafalski, M. and Lam, P. Y. S., Solid supported aryl/heteroaryl C-N cross-coupling reactions, Tetrahedron Lett., 40 (1999) 1623-1626.
6. (d) Kaiser, N. F., Bremberg, U., Larhed, M., Moberg, C. and Hallberg, A., Fast, convenient, and efficient molybdenum-catalyzed asymmetric allylic alkylations under noninertcConditions: An example of microwave-promoted fast chemistry, Angew. Chem., Int. Ed. Engl., 39 (2000) 3596-3598.
7. (e) Finaru, A., Berthault, A., Besson, T., Guillaumet, G. and Berteina-Raboin, S., Microwave-assisted solid-phase synthesis of 5-carboxamido-N-acetyltryptamine derivatives, Org. Lett. 4 (2002) 2613-2615.
8. For recent reviews on this reaction, see: (a) Hartwig, J. F., Palladium-Catalyzed Amination of Aryl Halides and Sulfonates, in Ricci, A. (ed.), Modern Amination Methods, Wiley-VCH, Weinheim, 2000, pp 195-262.
9. (b) Yang, B. H. and Buchwald, S. L., Palladium-catalyzed amination of aryl halides and sulfonates, J. Organomet. Chem., 576 (1999), 125-146.
10. (a) Ward, Y. D. and Farina, V., Solid phase synthesis of aryl amines via palladium-catalyzed amination of resin-bound aromatic bromides, Tetrahedron Lett., 37 (1996) 6993-6996.
11. (b) Willoughby, C. A. and Chapman, K. T., Solid phase synthesis of aryl amines, Tetrahedron Lett., 37 (1996) 7181-7184.
12. (c) Brill, W. K.-D., Riva-Toniolo, C. and Müller, S., Catalysis of 2- and 6-substitution reactions of purines on solid phase, Synlett, (2001) 1097-1100.
13. Weigand, K. and Pelka, S., Palladium-catalyzed amination of aryl halides on solid support, Org. Lett., 4 (2002) 4689-4692.
14. Two recent papers describe the application of microwave heating to the Pd-catalyzed aryl amination in solution: (a) Sharifi, A., Hosseinzadeh, R. and Mirzaei, M., Rapid microwave-induced palladium-catalyzed amination of aryl bromides, Monatsh. Chem., 133 (2002), 329-332.
15. (b) Wan, Y., Alterman, M. and Hallber, A., Palladium-catalyzed amination of aryl bromides using temperature-controlled microwave heating, Synthesis, (2002) 1597-1600.
16. SmithSynthesizer™and Emrys™Optimizer equipment from Personal Chemistry AB, Uppsala, Sweden was used in all our experiments.
17. Rink resin SS from Advanced ChemTech, Louisville, Kentucky, USA (Cat.-No. SA5030) was used. Resins from other suppliers gave lower and more variable results.