Palladium-catalyzed amination of aryl chlorides

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4807-4810

  Reddy, Nagavelli Prabhakar ^a   Tanaka, Masato ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; SYNTHESIS;

EID: 0030996347     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01038-1     Document Type: Article

References (14)

1. a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
2. b). Louie, J.; Hartwig, J. F. TretrahedronLett. 1995, 36, 3609-3612.
3. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133-1135.
4. Pd/dppf system was also used for amination of aryl bromides. See Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
5. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L.; J. Am. Chem. Soc. 1996, 118, 7215-7216.
6. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
7. a) For amino carbonylation, see Perry, R. J.; Wilson, B.D. J. Org. Chem., 1996, 61, 7482-7485.
8. b) For Heck arylation, see Reetz, M. T.; Lohmer, G. Chem. Commun. 1996, 1921-1922 and references cited therein.
9. 3 catalytic system for the synthesis of aryl piperazines and triaryl amines by treating aryl halides (bromides and chlorides) with piperazine and diaryl amines respectively.
10. 254, MERCK) using hexane/ether (4: 1) as eluent All the new products gave satisfactory spectral and analytical data.
11. a-Hydrogen-containing amines, when coordinated to a metal complex, tend to undergo dehydrogenation to produce imines and hydrido-metal species. The resulting hydrido-metal complex induces the hydrogenolysis of aryl halides. See ref. 1.
12. The details of these products will be published elsewhere.
13. For more details about the mechanism of amination of aryl bromides, see a) Paul, F.; Patt, J.; Hartwig, J. F. Organometallics, 1995, 14, 3030-3039.
14. b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109-13110