A Phosphine-mediated conversion of azides into diazo compounds

Angewandte Chemie - International Edition

Volumn 48, Issue 13, 2009, Pages 2359-2363

  Myers, Eddie L ^a   Raines, Ronald T ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Azides; Heterocycles; Phosphines; Staudinger reactionm; Synthetic methods

Indexed keywords

FUNCTIONAL GROUPS; PHOSPHORUS COMPOUNDS;

AZIDES; HETEROCYCLES; PHOSPHINES; STAUDINGER REACTIONM; SYNTHETIC METHODS;

NITROGEN COMPOUNDS;

AZIDE; AZO COMPOUND; PHOSPHINE; PHOSPHINE DERIVATIVE;

AZIDES; AZO COMPOUNDS; PHOSPHINES;

EID: 70349786390     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804689     Document Type: Article

References (58)

1. a) M. Regitz, G. Maas, Diazo Compounds: Properties and Synthesis,Academic Press, London, 1986, pp. 65-198;
2. b) A. Padwa, M. D. Weingarten, Chem. Rev. 1996, 96,223-269;
3. c) M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods forOrganic Synthesis with Diazo Compounds, Wiley, New York, 1998;
4. d) H. M. L. Davies, R. E. I Beckwith, Chem. Rev. 2003,103, 2861-2904;
5. e) Z. Zhang, J. Wang, Tetrahedron 2008, 64,6577-6605.
6. Q. R. Bartz, C. C. Elder, R. P. Frohardt, S. A. Fusari, T. H. Haskell, D.W. Johannessen, A. Ryder, Nature 1954, 173, 72-73.
7. a) S. Ito, T. Matsuya, S. Omura, M. Otani, A. Nakagawa, H. Takeshima, Y.Iwai, M. Ohtani, T. Hata, J. Antibiot. 1970, 23, 315-316;
8. b) S. J. Gould, N. Tamayo, C. R. Melville, M. C. Cone, J. Am. Chem.Soc. 1994, 116, 2207-2208;
9. c) S. Mithani, G. Weeratunga, N. J. Taylor, G. I. Dmitrienko, J. Am.Chem. Soc. 1994, 116, 2209-2210.
10. H. He, W.-D. Ding, V. S. Bernan, A. D. Richardson, CM. Ireland, M.Greenstein, G. A. Ellestad, G. T. Carter, J. Am. Chem. Soc. 2001,123, 5362-5363.
11. a) M. Regitz, Angew. Chem. 1967, 79, 786-801;
12. Angew. Chem. Int. Ed. Engl. 1967, 6, 733-749;
13. b) J.S. Baum, D. A. Shook, H. M. L. Davies, D. H. Smith, Synth.Commun. 1987, 17, 1709-1716.
14. a) T. Curtius, Ber. Dtsch. Chem. Ces. 1883, 16,2230-2231;
15. b) E. C. Horning, Organic Synthesis. Coll. Vol. 3, Wiley, NewYork, 1955, p. 392.
16. a) W. R. Bamford, T. S. Stevens, J. Chem. Soc. 1952,4735-4740;
17. b) J. R. Fulton, V. K. Aggarwal, J. de Vicente, Eur. J. Org. Chem.2005, 1479-1492.
18. a) T. L. Holton, H. Shechter, J. Org. Chem. 1995,60, 4725-4729;
19. b) M. E. Furrow, A. G. Myers, J. Am. Chem. Soc. 2004,126, 12222-12223.
20. T. J. De Boer, H. J. Backer, Organic Synthesis, Coll. Vol. 4,Wiley, New York, 1963, pp. 250-253.
21. a) R. J. Baumgarten, J. Org. Chem. 1967, 32,484-485;
22. b) M. Schroen, S. Bräse, Tetrahedron 2005, 61,12186-12192.
23. a) J. Kink, M. Regitz, Synthesis 1985, 569-585;
24. b) T. Ye, M. A. McKervey, Tetrahedron 1992, 48,8007-8022;
25. c) Y. Zhao, J. Wang, Synlett 2005, 2886-2892;
26. d) M. E. Meyer, E. M. Ferreira, B. M. Stoltz, Chem. Commun.2006, 1316-1318;
27. e) Y. Liu, Y. Zhang, N. Jee, M. P. Doyle, Org. Lett. 2008,10, 1605-1608.
28. D.B. Kimball, M. M. Haley, Angew. Chem. 2002, 114,3484-3498;
29. Angew. Chem. Int. Ed. 2002, 41, 3338-3351.
30. a) H. Wamhoff, G. Richardt, S. Stölben, Adv. Heterocycl.Chem. 1995, 33, 159-249;
31. b) P. M. Fresneda, P. Molina, Synlett 2004, 1197-1218.
32. a) P. Molina, C. López-Leonardo, J. Llamas-Botía, C.Foces-Foces, C. Fernández-Castaño, Tetrahedron 1996,52, 9629-9642;
33. b) M. Mizuno, I. Muramoto, K. Kobayashi, H. Yaginuma, T. Inazu,Synthesis 1999, 162-165;
34. c) M. D. Desamparados Ve-lasco, P. Molina, P. M. Fresneda, M. A. Sanz,Tetrahedron 2000, 56, 4079-4084;
35. d) J. A. Restituyo, L. R. Comstock, S. G. Peter son, T. Stringfellow, S.R. Rajski, Org. Lett. 2003, 5, 4357-4360;
36. e) X. Liu, N. Thirupathi, I. A. Guzei, J. G. Verkade, Inorg. Chem.2004, 43, 7431-7440;
37. f) A. Charafeddine, W. Dayoub, H. Chapuis, P. Strazewski, Chem. Eur.J. 2007, 13, 5566-5584,
38. a) E. Saxon, C. R. Bertozzi, Science 2000, 287,2007-2010;
39. b) B. L. Nilsson, L. L. Kiessling, R. T. Raines, Org. Lett.2000, 2, 1939-1941;
40. c) M. Kohn, R. Breinbauer, Angew. Chem. 2004, 116,3168-3178;
41. Angew. Chem. Int. Ed. 2004, 43, 3106-3116.
42. F. L. Lin, H. M. Hoyt, H. van Halbeek, R. G. Bergman, C. R. Bertozzi,J. Am. Chem. Soc. 2005, 127, 2686-2695.
43. a) G. Oddo, A. Algerino, Ber. Dtsch. Chem. Ges. B 1936,69, 279-282;
44. b) M. A. Kelly, M. Murray, M. L. Sinnott, J. Chem. Soc. Perkin Trans.2 1982, 1649-1654.
45. a) P. Krommes, J. Lorberth, J. Organomet. Chem. 1977,127, 19-31;
46. b) G. Wittig, W. Haag, Chem. Ber. 1955, 88,1654-1666;
47. c) H. Staudinger, J. Meyer, Helv. Chim. Acta 1919, 2,619-635.
48. a) J. L. Ozment, A. M. Schmeidekamp, L. A. Schultz-Merkel, R.H. Smith,Jr., C. J. Michejda, J. Am. Chem. Soc. 1991, 113, 397-405;
49. b) R.H. Smith, Jr., B. D. Wladkowski, J. A. Herling, T. D. Pfaltzgraff,B. Pruski, J. Klose, C. J. Michejda, J. Org. Chem. 1992,57, 654-661;
50. c) S. Erase, S. Dahmen, Chem. Eur. J. 2000, 6,1899-1905;
51. d) J. Rademann, J. Smerdka, G. Jung, P. Grosche, D. Schmid, Angew.Chem. 2001, 113, 390-393;
52. Angew. Chem. Int. Ed. 2001, 40, 381-385.
53. a) D. Y. Curtin, J. D. Druliner, J. Org. Chem. 1967,32, 1552-1557;
54. b) H. Lu, C. Li, Tetrahedron Lett. 2005, 46,5983-5985.
55. a) J. M. Antos, M. B. Francis, J. Am. Chem. Soc. 2004,126, 10256-10257;
56. b) A. Tarn, M. B. Soellner, R. T. Raines, J. Am. Chem. Soc.2007, 129, 11421-11430.
57. a) S. T. Laughlin, N. J. Agard, J. M. Baskin, I. S. Carrico, P. V. Chang,A. S. Ganguli, M. J. Hangauer, A. Lo, J. A. Prescher, C. R. Bertozzi,Methods Enzymol. 2006, 415, 230-250;
58. b) M Francis in Chemical Biology: From Small Molecules to SystemsBiology and Drug Design (Eds.: S. L. T. M. Kapoor, G. Wess), Wiley-VCH,Weinheim, 2007, pp. 593-634