Synthesis of arylpiperazines via palladium-catalyzed aromatic amination reaction with unprotected piperazines

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4463-4466

  Zhao, Shu Hai ^a   Miller, Aubry K ^a   Berger, Jacob ^a   Flippin, Lee A ^a  

^a ROCHE BIOSCIENCE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERAZINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; NONHUMAN; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0030600196     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00877-5     Document Type: Article

References (13)

1. 1. Broekkamp, C. L. E.; Leysen, D.B.; Peeters, W. M. M.; Pinder, R. M. J. Med. Chem. 1995, 38, 4615.
2. 2. (a) Kiristy, J. A.; Yung, D. K.; Mathony, D. E. J. Med. Chem. 1978, 21, 1301.
3. (b) Pollard; MacDowell, J. Am. Chem. Soc. 1934, 56, 2199.
4. 3. Mishani, E.; Dence, C. S.; McCarthy, T. J.; Welch, M. J. Tetrahedron Lett. 1996, 37, 319.
5. 4. (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1348.
6. (b) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
7. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
8. 5. (a) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
9. (b) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609.
10. (c) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708.
11. k1 Bisarylpiperazine
12. 3, 75MHz) δ (ppm) 19.9, 20.4, 46.1, 50.2, 50.6, 57.7, 116.5, 129.16, 129.6, 149.6. NOE experiments determined that the methyl group was attached to the 3 position of the piperazine ring and not the 2 position.
13. 1H NMR analysis.