A radical procedure for the anti-markovnikov hydroazidation of alkenes

Journal of the American Chemical Society

Volumn 133, Issue 35, 2011, Pages 13890-13893

  Kapat, Ajoy ^a   König, Andreas ^a   Montermini, Florian ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROBORATION; ONE-POT PROCEDURES; RADICAL INITIATORS; TRISUBSTITUTED ALKENES;

REGIOSELECTIVITY;

OLEFINS;

ALKENE DERIVATIVE; AZIDE; BORANE DERIVATIVE;

ANTIMARKOVNIKOV HYDROAZIDATION; ARTICLE; CHEMICAL MODIFICATION; CYCLOADDITION; HYDROBORATION; ONE POT SYNTHESIS; RADICAL REACTION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ALKENES; AZIDES; BORANES; STEREOISOMERISM;

EID: 80052305942     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2054989     Document Type: Article

References (58)

1. Doye, S. Sci. Synth. 2009, 40a, 241
2. Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795
3. Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579
4. Waser, J.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 8294
5. Waser, J.; Gaspar, B.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2006, 128, 11693
6. Hesp, K. D.; Stradiotto, M. ChemCatChem 2010, 2, 1192
7. Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2702
8. Kemper, J.; Studer, A. Angew. Chem., Int. Ed. 2005, 44, 4914
9. Guin, J.; Fröhlich, R.; Studer, A. Angew. Chem., Int. Ed. 2008, 47, 779
10. Guin, J.; Mück-Lichtenfeld, C.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2007, 129, 4498
11. Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237
12. Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646
13. Sreekumar, R.; Padmakumar, R.; Rugmini, P. Chem. Commun. 1997, 1133
14. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188
15. Organic Azides: Syntheses and Applications; Bräse, S.; Banert, K., Eds.; Wiley: Chichester, U.K., 2010.
16. Suzuki, A.; Dhillon, R. S. Top. Curr. Chem. 1986, 130, 23
17. Suzuki, A.; Sono, S.; Itoh, M.; Brown, H. C.; Midland, M. M. J. Am. Chem. Soc. 1971, 93, 4329
18. Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947
19. Carboni, B.; Vaultier, M. Bull. Soc. Chim. Fr. 1995, 132, 1003
20. Brown, H. C.; Midland, M. M.; Levy, A. B.; Suzuki, A.; Sono, S.; Itoh, M. Tetrahedron 1987, 43, 4079
21. Brown, H. C.; Kim, K. W.; Srebnik, M.; Singaram, B. Tetrahedron 1987, 43, 4071
22. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151
23. Felpin, F. X.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305
24. Salmon, A.; Carboni, B. J. Organomet. Chem. 1998, 567, 31
25. Brown, H. C.; Midland, M. M.; Levy, A. B. J. Am. Chem. Soc. 1973, 95, 2394
26. Brown, H. C.; Midland, M. M.; Levy, A. B. J. Am. Chem. Soc. 1972, 94, 2114
27. Jigajinni, V. B.; Pelter, A.; Smith, K. Tetrahedron Lett. 1978, 19, 181
28. Yang, R. Y.; Dai, L. X. Synthesis 1993, 481
29. Akimoto, I.; Suzuki, A. Synth. Commun. 1981, 11, 475
30. Genet, J. P.; Hajicek, J.; Bischoff, L.; Greck, C. Tetrahedron Lett. 1992, 33, 2677
31. Mueller, R. H. Tetrahedron Lett. 1976, 17, 2925
32. Suzuki, A.; Ishidoya, M.; Tabata, M. Synthesis 1976, 687
33. Masuda, Y.; Hoshi, M.; Arase, A. Bull. Chem. Soc. Jpn. 1984, 57, 1026
34. Ollivier, C.; Renaud, P. Angew. Chem., Int. Ed. 2000, 39, 925
35. Ollivier, C.; Renaud, P. Chem.-Eur. J. 1999, 5, 1468
36. Schaffner, A.-P.; Renaud, P. Eur. J. Org. Chem. 2004, 2291
37. Darmency, V.; Renaud, P. Top. Curr. Chem. 2006, 263, 71
38. Schaffner, A.-P.; Renaud, P. Angew. Chem., Int. Ed. 2003, 42, 2658
39. Schaffner, A.-P.; Becattini, B.; Ollivier, C.; Weber, V.; Renaud, P. Synthesis 2003, 2740
40. Schaffner, A. P.; Darmency, V.; Renaud, P. Angew. Chem., Int. Ed. 2006, 45, 5847
41. Schaffner, A. P.; Sarkunam, K.; Renaud, P. Helv. Chim. Acta 2006, 89, 2450
42. Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2001, 123, 4717
43. Panchaud, P.; Chabaud, L.; Landais, Y.; Ollivier, C.; Renaud, P.; Zigmantas, S. Chem.-Eur. J. 2004, 10, 3606
44. Nyfeler, E.; Renaud, P. Org. Lett. 2008, 10, 985
45. Renaud, P.; Ollivier, C.; Panchaud, P. Angew. Chem., Int. Ed. 2002, 41, 3460
46. Panchaud, P.; Renaud, P. Chimia 2004, 57, 232
47. Panchaud, P.; Renaud, P. J. Org. Chem. 2004, 69, 3205
48. Weidner, K.; Giroult, A.; Panchaud, P.; Renaud, P. J. Am. Chem. Soc. 2010, 132, 17511
49. Ortiz, M.; Larson, G. L. Synth. Commun. 1982, 12, 43
50. Garrett, C. E.; Fu, G. C. J. Org. Chem. 1996, 61, 3224
51. Cren, S.; Renaud, P. In e-EROS: Electronic Encyclopedia of Reagents for Organic Synthesis; Wiley, 2007.
52. da Silva Correa, C. M. M.; Lindsay, A. S.; Waters, W. A. J. Chem. Soc. C 1968, 1872
53. Kobayashi, M.; Tanaka, K.; Minato, H. Bull. Chem. Soc. Jpn. 1972, 45, 2906
54. Schaffner, A.-P.; Montermini, F.; Pozzi, D.; Darmency, V.; Scanlan, E. M.; Renaud, P. Adv. Synth. Catal. 2008, 350, 1163
55. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; Wiley-VCH: Weinheim, Germany, 1996; p 281.
56. Kono, H.; Ito, K.; Nagai, Y. Chem. Lett. 1975, 1095
57. Mannig, D.; Noth, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 878
58. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596