New rhodium-catalyzed amination reactions

Chemical Communications

Volumn , Issue 20, 1999, Pages 2029-2030

  Trauthwein, Harald ^a   Tillack, Annegret ^b   Beller, Matthias ^b  

^a SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; NORBORNADIENE DERIVATIVE; RHODIUM;

AMINATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 0033592560     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903920a     Document Type: Article

References (23)

1. For leading reviews of hydroamination, see: M. Beller and T. Müller, Chem. Rev., 1998, 98, 675; D. M. Roundhill, Chem. Rev. 1992, 92, 1; J.-J. Brunet, D. Neibecker and F. Niedercorn, J. Mol. Catal., 1989, 49, 235.
2. For leading reviews of hydroamination, see: M. Beller and T. Müller, Chem. Rev., 1998, 98, 675; D. M. Roundhill, Chem. Rev. 1992, 92, 1; J.-J. Brunet, D. Neibecker and F. Niedercorn, J. Mol. Catal., 1989, 49, 235.
3. For leading reviews of hydroamination, see: M. Beller and T. Müller, Chem. Rev., 1998, 98, 675; D. M. Roundhill, Chem. Rev. 1992, 92, 1; J.-J. Brunet, D. Neibecker and F. Niedercorn, J. Mol. Catal., 1989, 49, 235.
4. Recent examples: R. Dorta, P. Egli, F. Zürcher and A. Togni, J. Am. Chem. Soc., 1997, 119, 10 857; J.-J. Brunet, Gazz. Chim. Ital., 1997, 127, 111; V. M. Arrenodo, S. Tian, F. E. McDonald and T. J. Marks, J. Am. Chem. Soc., 1999, 121, 3633.
5. Recent examples: R. Dorta, P. Egli, F. Zürcher and A. Togni, J. Am. Chem. Soc., 1997, 119, 10 857; J.-J. Brunet, Gazz. Chim. Ital., 1997, 127, 111; V. M. Arrenodo, S. Tian, F. E. McDonald and T. J. Marks, J. Am. Chem. Soc., 1999, 121, 3633.
6. Recent examples: R. Dorta, P. Egli, F. Zürcher and A. Togni, J. Am. Chem. Soc., 1997, 119, 10 857; J.-J. Brunet, Gazz. Chim. Ital., 1997, 127, 111; V. M. Arrenodo, S. Tian, F. E. McDonald and T. J. Marks, J. Am. Chem. Soc., 1999, 121, 3633.
7. D. R. Coulson, Tetrahedron Lett., 1971, 12, 429.
8. J.-J. Brunet, D. Neibecker and K. Philippot, J. Chem. Soc., Chem. Commun., 1992, 1215; Tetrahedron Lett., 1993, 34, 3877; J.-J. Brunet, G. Commenges, D. Neibecker and K. Philippot, J. Organomet. Chem., 1994, 469, 221.
9. J.-J. Brunet, D. Neibecker and K. Philippot, J. Chem. Soc., Chem. Commun., 1992, 1215; Tetrahedron Lett., 1993, 34, 3877; J.-J. Brunet, G. Commenges, D. Neibecker and K. Philippot, J. Organomet. Chem., 1994, 469, 221.
10. J.-J. Brunet, D. Neibecker and K. Philippot, J. Chem. Soc., Chem. Commun., 1992, 1215; Tetrahedron Lett., 1993, 34, 3877; J.-J. Brunet, G. Commenges, D. Neibecker and K. Philippot, J. Organomet. Chem., 1994, 469, 221.
11. M. Beller, M. Eichberger and H. Trauthwein, Angew. Chem., Int. Ed. Engl., 1997, 36, 2225; M. Beller, M. Eichberger and H. Trauthwein, Catalysis of Organic Reactions, ed. F. Herkes, Marcel Dekker, New York, 1998; M. Beller, H. Trauthwein, M. Eichberger, J. Herwig, T. E. Müller and O. Thiel, Eur. J. Chem., 1999, 5, 1306; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, T. E. Müller and A. Zapf, J. Organomet. Chem., 1998, 566, 277; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl and T. E. Müller, Eur. J. Inorg. Chem., 1999, 1121.
12. M. Beller, M. Eichberger and H. Trauthwein, Angew. Chem., Int. Ed. Engl., 1997, 36, 2225; M. Beller, M. Eichberger and H. Trauthwein, Catalysis of Organic Reactions, ed. F. Herkes, Marcel Dekker, New York, 1998; M. Beller, H. Trauthwein, M. Eichberger, J. Herwig, T. E. Müller and O. Thiel, Eur. J. Chem., 1999, 5, 1306; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, T. E. Müller and A. Zapf, J. Organomet. Chem., 1998, 566, 277; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl and T. E. Müller, Eur. J. Inorg. Chem., 1999, 1121.
13. M. Beller, M. Eichberger and H. Trauthwein, Angew. Chem., Int. Ed. Engl., 1997, 36, 2225; M. Beller, M. Eichberger and H. Trauthwein, Catalysis of Organic Reactions, ed. F. Herkes, Marcel Dekker, New York, 1998; M. Beller, H. Trauthwein, M. Eichberger, J. Herwig, T. E. Müller and O. Thiel, Eur. J. Chem., 1999, 5, 1306; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, T. E. Müller and A. Zapf, J. Organomet. Chem., 1998, 566, 277; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl and T. E. Müller, Eur. J. Inorg. Chem., 1999, 1121.
14. M. Beller, M. Eichberger and H. Trauthwein, Angew. Chem., Int. Ed. Engl., 1997, 36, 2225; M. Beller, M. Eichberger and H. Trauthwein, Catalysis of Organic Reactions, ed. F. Herkes, Marcel Dekker, New York, 1998; M. Beller, H. Trauthwein, M. Eichberger, J. Herwig, T. E. Müller and O. Thiel, Eur. J. Chem., 1999, 5, 1306; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, T. E. Müller and A. Zapf, J. Organomet. Chem., 1998, 566, 277; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl and T. E. Müller, Eur. J. Inorg. Chem., 1999, 1121.
15. M. Beller, M. Eichberger and H. Trauthwein, Angew. Chem., Int. Ed. Engl., 1997, 36, 2225; M. Beller, M. Eichberger and H. Trauthwein, Catalysis of Organic Reactions, ed. F. Herkes, Marcel Dekker, New York, 1998; M. Beller, H. Trauthwein, M. Eichberger, J. Herwig, T. E. Müller and O. Thiel, Eur. J. Chem., 1999, 5, 1306; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, T. E. Müller and A. Zapf, J. Organomet. Chem., 1998, 566, 277; M. Beller, H. Trauthwein, M. Eichberger, C. Breindl and T. E. Müller, Eur. J. Inorg. Chem., 1999, 1121.
16. L. Schmerling, J. P. Luvisi and R. W. Welak, J. Am. Chem. Soc., 1956, 78, 2819; J. Kiji, S. Nishimura, S. Yoshikawa, E. Sasakawa and J. Furukawa, Bull. Chem. Soc. Jpn., 1974, 47, 2523.
17. L. Schmerling, J. P. Luvisi and R. W. Welak, J. Am. Chem. Soc., 1956, 78, 2819; J. Kiji, S. Nishimura, S. Yoshikawa, E. Sasakawa and J. Furukawa, Bull. Chem. Soc. Jpn., 1974, 47, 2523.
18. 3-MeOH = 30:1). Isolated yields: 3a: 32% (252 mg); 3b: 40% (312 mg); 3c: 37% (266 mg); 3d: 34% (268 mg); 4c: 4% (23 mg).
19. We term this reaction of amines with norbornadiene a pseudo-1,3-addition in agreement with literature for 1,4-addition reactions.
20. A. G. Cook, M. L. Absi and V. K. Bowden, J. Org. Chem., 1995, 60, 3169.
21. G. D. Diana and F. Pancic, Angew. Chem., 1976, 88, 458; E. X. Albuquerque, A. T. Eldefrawi, M. E. Eldefrawi, N. A. Mansour and M.-C. Tsai, Science, 1978, 199, 788; Negwer, Organic-chemical Drugs and their Synonyms, Fachinformationszentrum Chemie, Berlin.
22. G. D. Diana and F. Pancic, Angew. Chem., 1976, 88, 458; E. X. Albuquerque, A. T. Eldefrawi, M. E. Eldefrawi, N. A. Mansour and M.-C. Tsai, Science, 1978, 199, 788; Negwer, Organic-chemical Drugs and their Synonyms, Fachinformationszentrum Chemie, Berlin.
23. G. D. Diana and F. Pancic, Angew. Chem., 1976, 88, 458; E. X. Albuquerque, A. T. Eldefrawi, M. E. Eldefrawi, N. A. Mansour and M.-C. Tsai, Science, 1978, 199, 788; Negwer, Organic-chemical Drugs and their Synonyms, Fachinformationszentrum Chemie, Berlin.