Solid phase synthesis of aryl amines via palladium catalyzed amination of resin-bound aromatic bromides

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 6993-6996

  Ward, Yancey D ^a   Farina, Vittorio ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BENZAMIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030599273     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01566-3     Document Type: Article

References (11)

1. 1. (a) Ellman J. A.; Thompson, L. A. Chem. Rev. 1996, 96, 555-560;
2. (b) Fruchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 1742 and references contained therein.
3. 2. (a) Buchwald, S. L.; Guram, A. S.; Rennels, R. A. Angew. Chem. Int. Ed. Engl. 1995, 34, 1348-1350;
4. (b) Hartwig, J. F; Louie, J. Tetrahedron Lett., 1995, 36, 3609.
5. 3. Polystyrene Rink resin (loading of 0.82 mmol per gram) was purchased from Advanced ChemTech.
6. 4. The aromatic bromides used in this study were purchased from Aldrich and used without further purification. The substrates were attached to Rink resin through coupling with N,N-diisopropylcarbodiimide and DMAP. Cleavage of the substrates from the resins and weighing the dry residues confirmed the quantitative reaction of the free amino groups.
7. 1H NMR and MS. In every case the yields were determined to be essentially quantitative based on the mass of the recovered material.
8. 6. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. in press. We thank Prof. Buchwald for sharing his results prior to publication.
9. 7. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. in press.
10. 8. The following amines could not be coupled under any of the conditions tried: Ortho-and paranitroaniline, aminotriazine, 5-aminouracil, 2,6-diaminoanthraquinone, histidine, 2-aminobenzimidazole, imidazole, and pyrazole.
11. 3/Pd or BINAP/Pd would not have been successful in these cases.