Tin-free radical carboazidation

Chimia

Volumn 58, Issue 4, 2004, Pages 232-233

  Panchaud, Philippe ^a   Renaud, Philippe ^b  

^a UNIVERSITY OF BERN   (Switzerland)

^b NONE

Author keywords

Amination; Azides; Radicals; Synthetic methods; Tin free

Indexed keywords

3 PYRIDINESULFONYL AZIDE; ALKENE DERIVATIVE; AZIDE; BENZENE DERIVATIVE; BENZENESULFONYL AZIDE; PYRIDINE DERIVATIVE; RADICAL; TIN; UNCLASSIFIED DRUG;

AMINATION; CHEMICAL REACTION; CONFERENCE PAPER; PURIFICATION; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 2442503309     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/000942904777677920     Document Type: Conference Paper

References (24)

1. P. Panchaud, C. Ollivier, P. Renaud, S. Zigmantas, J. Org. Chem. 2004, 69, in press.
2. P. Renaud, C. Ollivier, P. Panchaud, Angew. Chem., Int. Ed. 2002, 41, 3460.
3. For general reviews on radical reactions, see: a) 'Radicals in Organic Synthesis', Eds. P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, 2001; b) B. Giese, 'Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds', Pergamon, Oxford, 1988; c) D.P. Curran in 'Comprehensive Organic Synthesis', Vol. 4, Eds. B. M. Trost, I. Fleming, M. F. Semmelhack, Pergamon, Oxford, 1991, p. 715 and 779; d) W.B. Motherwell, D. Crich, 'Free Radical Chain Reactions in Organic Synthesis', Academic Press, London, 1992; e) J. Fossey, D. Lefort, J. Sorba, 'Free Radicals in Organic Synthesis', Wiley, Chichester, 1995; f) C. Chatgilialoglu, P. Renaud in 'General Aspects of the Chemistry of Radicals', Ed. Z.B. Alfassi, Wiley, Chichester, 1999, p. 501.
4. For general reviews on radical reactions, see: a) 'Radicals in Organic Synthesis', Eds. P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, 2001; b) B. Giese, 'Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds', Pergamon, Oxford, 1988; c) D.P. Curran in 'Comprehensive Organic Synthesis', Vol. 4, Eds. B. M. Trost, I. Fleming, M. F. Semmelhack, Pergamon, Oxford, 1991, p. 715 and 779; d) W.B. Motherwell, D. Crich, 'Free Radical Chain Reactions in Organic Synthesis', Academic Press, London, 1992; e) J. Fossey, D. Lefort, J. Sorba, 'Free Radicals in Organic Synthesis', Wiley, Chichester, 1995; f) C. Chatgilialoglu, P. Renaud in 'General Aspects of the Chemistry of Radicals', Ed. Z.B. Alfassi, Wiley, Chichester, 1999, p. 501.
5. For general reviews on radical reactions, see: a) 'Radicals in Organic Synthesis', Eds. P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, 2001; b) B. Giese, 'Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds', Pergamon, Oxford, 1988; c) D.P. Curran in 'Comprehensive Organic Synthesis', Vol. 4, Eds. B. M. Trost, I. Fleming, M. F. Semmelhack, Pergamon, Oxford, 1991, p. 715 and 779; d) W.B. Motherwell, D. Crich, 'Free Radical Chain Reactions in Organic Synthesis', Academic Press, London, 1992; e) J. Fossey, D. Lefort, J. Sorba, 'Free Radicals in Organic Synthesis', Wiley, Chichester, 1995; f) C. Chatgilialoglu, P. Renaud in 'General Aspects of the Chemistry of Radicals', Ed. Z.B. Alfassi, Wiley, Chichester, 1999, p. 501.
6. For general reviews on radical reactions, see: a) 'Radicals in Organic Synthesis', Eds. P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, 2001; b) B. Giese, 'Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds', Pergamon, Oxford, 1988; c) D.P. Curran in 'Comprehensive Organic Synthesis', Vol. 4, Eds. B. M. Trost, I. Fleming, M. F. Semmelhack, Pergamon, Oxford, 1991, p. 715 and 779; d) W.B. Motherwell, D. Crich, 'Free Radical Chain Reactions in Organic Synthesis', Academic Press, London, 1992; e) J. Fossey, D. Lefort, J. Sorba, 'Free Radicals in Organic Synthesis', Wiley, Chichester, 1995; f) C. Chatgilialoglu, P. Renaud in 'General Aspects of the Chemistry of Radicals', Ed. Z.B. Alfassi, Wiley, Chichester, 1999, p. 501.
7. For general reviews on radical reactions, see: a) 'Radicals in Organic Synthesis', Eds. P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, 2001; b) B. Giese, 'Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds', Pergamon, Oxford, 1988; c) D.P. Curran in 'Comprehensive Organic Synthesis', Vol. 4, Eds. B. M. Trost, I. Fleming, M. F. Semmelhack, Pergamon, Oxford, 1991, p. 715 and 779; d) W.B. Motherwell, D. Crich, 'Free Radical Chain Reactions in Organic Synthesis', Academic Press, London, 1992; e) J. Fossey, D. Lefort, J. Sorba, 'Free Radicals in Organic Synthesis', Wiley, Chichester, 1995; f) C. Chatgilialoglu, P. Renaud in 'General Aspects of the Chemistry of Radicals', Ed. Z.B. Alfassi, Wiley, Chichester, 1999, p. 501.
8. For general reviews on radical reactions, see: a) 'Radicals in Organic Synthesis', Eds. P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, 2001; b) B. Giese, 'Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds', Pergamon, Oxford, 1988; c) D.P. Curran in 'Comprehensive Organic Synthesis', Vol. 4, Eds. B. M. Trost, I. Fleming, M. F. Semmelhack, Pergamon, Oxford, 1991, p. 715 and 779; d) W.B. Motherwell, D. Crich, 'Free Radical Chain Reactions in Organic Synthesis', Academic Press, London, 1992; e) J. Fossey, D. Lefort, J. Sorba, 'Free Radicals in Organic Synthesis', Wiley, Chichester, 1995; f) C. Chatgilialoglu, P. Renaud in 'General Aspects of the Chemistry of Radicals', Ed. Z.B. Alfassi, Wiley, Chichester, 1999, p. 501.
9. a) P. A. Baguley, J. C. Walton, Angew. Chem. Int. Ed. 1998, 37, 3072; b) A. Studer, S. Amrein, Synthesis 2002, 835.
10. a) P. A. Baguley, J. C. Walton, Angew. Chem. Int. Ed. 1998, 37, 3072; b) A. Studer, S. Amrein, Synthesis 2002, 835.
11. P. Panchaud, P. Renaud, submitted.
12. C. Ollivier, P. Renaud, J. Am. Chem. Soc. 2000, 722, 6496.
13. C. Ollivier, P. Renaud, J. Am. Chem. Soc. 2001, 723, 4717.
14. K. Nozaki, K. Oshima, K. Uchimoto, J. Am. Chem. Soc. 1987, 109, 2547.
15. H. Yorimitsu, K. Oshima in 'Radicals in Organic Synthesis', Vol. 1, Eds. P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, 2001, pp. 11.
16. Y. Ichinose, S. Matsunaga, K. Fugami, K. Oshima, K. Utimoto, Tetrahedron Lett. 1989, 30, 3155.
17. E. Baciocchi, E. Muraglia, Tetrahedron Lett. 1994, 35, 2763.
18. H. Yorimitsu, H. Shinokubo, K. Oshima, Synlett 2002, 674.
19. P. Panchaud, P. Renaud, J. Org. Chem. 2004, 69, in press.
20. a) A.G. Davies, BP. Roberts, Acc. Chem. Res. 1972, 5, 387; b) A. G. Davies, B.P. Roberts, B.R. Sanderson, J. Chem. Soc., Perkin Trans. 2 1973, 626.
21. a) A.G. Davies, BP. Roberts, Acc. Chem. Res. 1972, 5, 387; b) A. G. Davies, B.P. Roberts, B.R. Sanderson, J. Chem. Soc., Perkin Trans. 2 1973, 626.
22. 3B-induced azidation was also examined. Surprisingly, their conversion into azides proved to be less efficient than under the previously reported ditin conditions. For example, carboazidation of 1-octene was achieved in 51 % yield only starting from 2-ethoxythiocarbonyl-sulfanylethanoate.
23. The iodomalonate 7 has to be freshly prepared in order to give reproducible yields.
24. D.P. Curran, M.H. Chen, E. Spletzer, C.M. Seong, C.T. Chang, J. Am. Chem. Soc. 1989, 111, 8872.