Conversion of azides into diazo compounds in water

Journal of the American Chemical Society

Volumn 135, Issue 40, 2013, Pages 14936-14939

  Chou, Ho Hsuan ^a   Raines, Ronald T ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDO GROUP; CHEMICAL BIOLOGY; DESIGN AND OPTIMIZATION; DIAZO COMPOUNDS; NEUTRAL PH; PHOSPHATE BUFFERS; REACTION PROGRESS; SYNTHETIC ORGANIC CHEMISTRY;

BIOPOLYMERS;

AZIDE; BIOPOLYMER; ERBIUM; FUNCTIONAL GROUP; LIGAND; PHOSPHATE; WATER;

ARTICLE; BIOLOGY; COLORIMETRY; ELECTROPHILICITY; NUCLEOPHILICITY; ORGANIC CHEMISTRY; PH; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

AZIDES; AZO COMPOUNDS; SUBSTRATE SPECIFICITY; WATER;

EID: 84885591249     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja407822b     Document Type: Article

References (67)

1. Padwa, A., Ed. 1,3-Dipolar Cycloaddition Chemistry; John Wiley & Sons: Hoboken, NJ, 1984.
2. Padwa, A.; Pearson, W. H., Eds. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; John Wiley & Sons: Hoboken, NJ, 2002.
3. Dahn, H.; Diderich, G. Helv. Chim. Acta 1971, 54, 1950-1960
4. Regitz, M.; Maas, G. Diazo Compounds: Properties and Synthesis; Academic Press: New York, 1986.
5. Johnston, J. N.; Muchalski, H.; Troyer, T. L. Angew. Chem., Int. Ed. 2010, 49, 2290-2298
6. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453
7. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223-269
8. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-935
9. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861-2903
10. Wee, A. G. H. Curr. Org. Synth. 2006, 3, 499-555
11. Ferreira, V. F. Curr. Org. Synth. 2007, 11, 177-193
12. Chibnall, A. C.; Mangan, J. L.; Rees, M. W. Biochem. J. 1958, 68, 114-118
13. Doscher, M. S.; Wilcox, P. E. J. Biol. Chem. 1961, 236, 1328-1337
14. Riehm, J. P.; Scheraga, H. A. Biochemistry 1965, 4, 772-782
15. Antos, J. M.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 10256-10257
16. Antos, J. M.; McFarland, J. M.; Iavarone, A. T.; Francis, M. B. J. Am. Chem. Soc. 2009, 131, 6301-6308
17. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2012, 46, 236-247
18. Ball, Z. T. Acc. Chem. Res. 2012, 46, 560-570
19. Chen, Z.; Vohidov, F.; Coughlin, J. M.; Stagg, L. J.; Arold, S. T.; Ladbury, J. E.; Ball, Z. T. J. Am. Chem. Soc. 2012, 134, 10138-10145
20. McGrath, N. A.; Raines, R. T. Chem. Sci. 2012, 3, 3237-3240
21. Curtius, T. Ber. Dtsch. Chem. Ges. 1890, 23, 3023-3033
22. Curtius, T. J. Prakt. Chem. 1894, 50, 275-294
23. Curtius, T. Ber. Dtsch. Chem. Ges. 1883, 16, 2230-2231
24. Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Commun. 1987, 17, 1709-1716
25. Holton, T. L.; Shechter, H. J. Org. Chem. 1995, 60, 4725-4729
26. Furrow, M. E.; Myers, A. G. J. Am. Chem. Soc. 2004, 126, 12222-12223
27. Fulton, J. R.; Aggarwal, V. K.; de Vicente, J. Eur. J. Org. Chem. 2005, 1479-1492
28. Myers, E. L.; Raines, R. T. Angew. Chem., Int. Ed. 2009, 48, 2359-2363
29. Maas, G. Angew. Chem., Int. Ed. 2009, 48, 8186-8195
30. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137
31. Debets, M. F.; van der Doelen, C. W.; Rutjes, F. P.; van Delft, F. L. ChemBioChem 2010, 11, 1168-1184
32. Jewett, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272-1279
33. Schilling, C. I.; Jung, N.; Biskup, M.; Schepers, U.; Bräse, S. Chem. Soc. Rev. 2011, 40, 4840-4871
34. El-Sagheer, A. H.; Brown, T. Acc. Chem. Res. 2012, 45, 1258-1267
35. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635-646
36. Nilsson, B. L.; Kiessling, L. L.; Raines, R. T. Org. Lett. 2000, 3, 9-12
37. Nilsson, B. L.; Kiessling, L. L.; Raines, R. T. Org. Lett. 2000, 2, 1939-1941
38. Tam, A.; Soellner, M. B.; Raines, R. T. J. Am. Chem. Soc. 2007, 129, 11421-11430
39. Tam, A.; Raines, R. T. Bioorg. Med. Chem. 2009, 17, 1055-1063
40. Kremers, J. A.; Meijer, E. W. J. Org. Chem. 1994, 59, 4262-4266
41. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4 th ed.; John Wiley & Sons: Hoboken, NJ, 2006.
42. Stankevič, M.; Pietrusiewicz, K. M. Synlett 2003, 1012-1016
43. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244-5252
44. Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur. J. Org. Chem. 2006, 2006, 29-49
45. Van Overschelde, M.; Vervecken, E.; Modha, S. G.; Cogen, S.; Van der Eycken, E.; Van der Eycken, J. Tetrahedron 2009, 65, 6410-6415
46. Biggs, A. I. Trans. Faraday Soc. 1954, 50, 800-802
47. Levine, M. N.; Lavis, L. D.; Raines, R. T. Molecules 2008, 13, 204-211
48. Fourteau, L.; Benoist, E.; Dartiguenave, M. Synlett 2001, 1, 126-128
49. Ishikawa, F.; Tsumuraya, T.; Fujii, I. J. Am. Chem. Soc. 2008, 131, 456-457
50. Yam, M.; Chong, J. H.; Tsang, C.-W.; Patrick, B. O.; Lam, A. E.; Gates, D. P. Inorg. Chem. 2006, 45, 5225-5234
51. Bates, J. I.; Patrick, B. O.; Gates, D. P. New J. Chem. 2010, 34, 1660-1666
52. Yavari, I.; Alizadeh, A.; Anary-Abbasinejad, M. Tetrahedron Lett. 2003, 44, 2877-2879
53. Castañeda, F.; Aliaga, C.; Acuña, C.; Silva, P.; Bunton, C. A. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 1188-1208
54. Wube, A. A.; Hüfner, A.; Thomaschitz, C.; Blunder, M.; Kollroser, M.; Bauer, R.; Bucar, F. Bioorg. Med. Chem. Lett. 2011, 19, 567-579
55. Pettersson, B.; Hasimbegovic, V.; Bergman, J. J. Org. Chem. 2011, 76, 1554-1561
56. Rüegg, U. T.; Rudinger, J. Methods Enzymol. 1977, 47, 111-116
57. Cline, D. J.; Redding, S. E.; Brohawn, S. G.; Psathas, J. N.; Schneider, J. P.; Thorpe, C. Biochemistry 2004, 43, 15195-15203
58. Scales, C. W.; Convertine, A. J.; McCormick, C. L. Biomacromolecules 2006, 7, 1389-1392
59. Hanusek, J.; Russell, M. A.; Laws, A. P.; Jansa, P.; Atherton, J. H.; Fettes, K.; Page, M. I. Org. Biomol. Chem. 2007, 5, 478-484
60. Jones, M. W.; Strickland, R. A.; Schumacher, F. F.; Caddick, S.; Baker, J. R.; Gibson, M. I.; Haddleton, D. M. J. Am. Chem. Soc. 2011, 134, 1847-1852
61. Fox, D. L.; Robinson, A. A.; Frank, J. B.; Salvatore, R. N. Tetrahedron Lett. 2003, 44, 7579-7582
62. Azizi, N.; Saidi, M. R. Tetrahedron Lett. 2003, 44, 7933-7935
63. El-Sawi, E. A.; Mostafa, T. B.; Radwan, H. A. Chem. Heterocycl. Compd. 2009, 45, 981-989
64. Fernández-Pérez, H.; Donald, S. M. A.; Munslow, I. J.; Benet-Buchholz, J.; Maseras, F.; Vidal-Ferran, A. Chem.-Eur. J. 2010, 16, 6495-6508
65. Raines, R. T. Chem. Rev. 1998, 98, 1045-1065
66. Marshall, G. R.; Feng, J. A.; Kuster, D. J. Biopolymers 2008, 90, 259-277
67. Cuchillo, C. M.; Nogués, M. V.; Raines, R. T. Biochemistry 2011, 50, 7835-7841