Oxidative and reductive carbodiazenylation of nonactivated olefins

Journal of Organic Chemistry

Volumn 72, Issue 2, 2007, Pages 476-484

  Heinrich, Markus R ^a   Blank, Olga ^a   Wetzel, Alexander ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLDIAZONIUM SALTS; CARBODIAZENYLATION; HETEROCYCLIC STRUCTURES; VALUABLE PRECURSORS;

AMINES; AMINO ACIDS; CARBONIZATION; KETONES; REDOX REACTIONS; SALTS;

OLEFINS;

ALKENE; BETA AMINO ACID DERIVATIVE; DIAZONIUM COMPOUND; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CARBOAMINATION; CARBODIAZENYLATION; CHEMICAL REACTION KINETICS; OXIDATION REDUCTION REACTION; SYNTHESIS;

EID: 33846204009     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061919p     Document Type: Article

References (82)

1. Al Adel, I.; Salami, B. A.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 934-938.
2. For Meerwein arylation, see: Rondestvedt, C. S. Org. React. 1976, 24, 225-259.
3. Zollinger, H. Color Chemistry: syntheses, properties and applications of organic dyes and pigments; Wiley-VCH: Weinheim, New York, 1987.
4. (a) Phillips, R. R. Org. React. 1959, 10, 143-178.
5. (b) Yao, H. C.; Resnick, P. J. Am. Chem. Soc. 1962, 84, 3514-3517.
6. Kozikowski, A. P.; Floyd, W. C. Tetrahedron Lett. 1978, 19, 19-22.
7. (a) Galli, C. Chem. Rev. 1988, 88, 765-792.
8. (b) Galli, C. J. Chem. Soc., Perkin Trans 2 1984, 897-902.
9. Citterio, A.; Minisci, F.; Albinati, A.; Bruckner, S. Tetrahedron Lett. 1980, 21, 2909-2910.
10. Citterio, A.; Ramperti, M.; Vismara, E. J. Heterocycl. Chem. 1981, 18, 763-766.
11. (a) Citterio, A.; Minisci, F.; Vismara, E. J. Org. Chem. 1982, 47, 81-88.
12. (b) Citterio, A.; Minisci, F. J. Org. Chem. 1982, 47, 1759-1761.
13. Minisci, F.; Coppa, F.; Fontana, F.; Pianese, G.; Zhao, L. J. Org. Chem. 1992, 57, 3929-3933.
14. Heinrich, M. R.; Blank, O.; Wölfel, S. Org. Lett. 2006, 8, 3323-3325.
15. (a) Blank, O.; Heinrich, M. R. Eur. J. Org. Chem. 2006, 4331-4334;
16. (b) Heinrich, M. R.; Blank, O.; Wetzel, A. Synlett 2006, 3352-3354.
17. (a) Adlington, R. M.; Baldwin, J. E.; Bottaro, J. C.; Perry, M. W. D. J. Chem. Soc., Chem. Commun. 1983, 1040-1041.
18. (b) Baldwin, J. E.; Bottaro, J. C.; Kolhe, J. N.; Adlington, R. M. J. Chem. Soc., Chem. Commun. 1984, 22-23.
19. Baldwin, J. E.; Adlington, R. M.; Bottaro, J. C.; Jain, A. U.; Kolhe, J. N.; Perry, M. W. D.; Newington, I. M. J. Chem. Soc., Chem. Commun. 1984, 1095-1096.
20. Baldwin, J. E.; Adlington, R. M.; Jain, A. U.; Kolhe, J. N.; Perry, M. W. D. Tetrahedron 1986, 42, 4247-4252.
21. (a) Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2000, 122, 6496-6497.
22. (b) Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2001, 123, 4717-4727.
23. Panchaud, P.; Renaud, P. J. Org. Chem. 2004, 69, 3205-3207.
24. Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas, S. J. Org. Chem. 2004, 69, 2755-2759.
25. (a) Chabaud, L.; Landais, Y.; Renaud, P. Org. Lett. 2005, 7, 2587-2590.
26. (b) Chabaud, L.; Landais, Y.; Renaud, P. Org. Lett. 2002, 4, 4257-4260.
27. Barton, D. H. R.; Jaszberenyi, J. C.; Theodorakis, E. A.; Reibenspies, J. H. J. Am. Chem. Soc. 1993, 115, 8050-8059.
28. Girard, P.; Guillot, N.; Motherwell, W. B.; Potier, P. Chem. Commun. 1995, 2385-2386.
29. Baigrie, B. D.; Cadogan, J. I. G.; Sharp, J. T. J. Chem. Soc., Perkin Trans. 1 1975, 1065-1067.
30. (a) Nakhla, J. S.; Kampf, J. W.; Wolfe, J. P. J. Am. Chem. Soc. 2006, 128, 2893-2901.
31. (b) Ney, J. E.; Hay, M. B.; Yang, Q.; Wolfe, J. P. Adv. Synth. Catal. 2005, 347, 1614-1620.
32. Yang, Q.; Ney, J. E.; Wolfe, J. P. Org. Lett. 2005, 7, 2575-2578.
33. Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024-15025.
34. Kamijo, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 3230-3233.
35. Ruck, R. T.; Zuckerman, R. L.; Krska, S. W.; Bergman, R. G. Angew. Chem., Int. Ed. 2004, 43, 5372-5374.
36. Basuli, F.; Aneetha, H.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc. 2005, 127, 17992-17993.
37. Lang, M.; Spiteller, P.; Hellwig, V.; Steglich, W. Angew. Chem., Int. Ed. 2001, 40, 1704-1705.
38. Kühle, E.; Klauke, E.; Frohberger, P. E.; Bayer, A. G. Ger. Pat. 2712434, 1978.
39. For the oxidative degradation of 1-acyl-2-arylhydrazines, see: (a) Bowman, W. R.; Forshaw, J. A.; Hall, K. P.; Kitchin, J. P.; Mott, A. W. Tetrahedron 1996, 52, 3961-3972.
40. (b) Milne, H. B.; Kilday, W. J. Org. Chem. 1965, 30, 64-66.
41. Völkert, M.; Koul, S.; Müller, G. H.; Lehnig, M.; Waldmann, H. J. Org. Chem. 2002, 67, 6902-6910.
42. For stability of aryl diazenes, see: (a) Cohen, S. G.; Nicholson, J. J. Org. Chem. 1965, 30, 1162-1168.
43. (b) Cohen, S. G.; Nicholson, J. J. Am. Chem. Soc. 1966, 88, 2247-2252.
44. Huang, P. C.; Kosower, E. M. J. Am. Chem. Soc. 1967, 89, 3910-3911.
45. (a) Postowsky, I. J.; Lugowkin, B. P.; Mandryk, G. F. Chem. Ber. 1936, 69, 1913-1915.
46. (b) Chattaway, F. D. J. Chem. Soc. 1908, 93, 952-960.
47. Charrier, G. Gazz. Chim. Ital. 1915, 45, 516-523.
48. Nakano, S.; Enoki, H.; Kawashima, T. Chem. Lett. 1980, 1173-1176.
49. (e) Hoffman, R. V.; Kumar, A. J. Org. Chem. 1984, 49, 4014-4017.
50. (f) Pütter, R. Houben-Weyl, Methoden der Organischen Chemie, 4. Auflage, Band X/3, 78-83.
51. Hauser, C. R.; Breslow, D. S. J. Am. Chem. Soc. 1941, 63, 418-420.
52. Alarcón, S. H.; Olivieri, A. C.; Sanz, D.; Claramunt, R. M.; Elguero, J. J. Mol. Struct. 2004, 705, 1.
53. . (ref a).
54. (a) Bunnett, J. F.; Yijima, C. J. Org. Chem. 1977, 42, 639-643.
55. (b) Tröndlin, F.; Rüchardt, C. Chem. Ber. 1977, 110, 2494.
56. Broxton, T. J.; Bunnett, J. F.; Paik, C. H. J. Org. Chem. 1977, 42, 643-649.
57. DeTar, D. F.; Turetzky, M. N. J. Am. Chem. Soc. 1955, 77, 1745-1750.
58. (e) DeTar, D. F.; Kosuge, T. J. Am. Chem. Soc. 1958, 80, 6072-6077.
59. (f) Bunnett, J. F.; Takayama, H. J. Org. Chem. 1968, 33, 1924-1928.
60. (g) Pazo-Llorente, R.; Maskill, H.; Bravo-Diaz, C.; Gonzalez-Romero, E.; Eur. J. Org. Chem. 2006, 2201-2209.
61. Dediazoniation of aryldiazonium ions in various solvents: (a) DMF: Markgraf, J. H.; Chang, R.; Cort, J. R.; Durant, J. L.; Finkelstein, M.; Gross, A. W.; Lavyne, M. H.; Moore, W. M.; Petersen, R. C.; Ross, S. D. Tetrahedron 1997, 53, 10009-10018.
62. (b) Wassmundt, F. W.; Kiesman, W. F.; J. Org. Chem. 1997, 62, 8304-8308.
63. Pazo-Llorente, R.; Bravo-Diaz, C.; Gonzalez-Romero, E. Eur. J. Org. Chem. 2003, 3421-3428.
64. Synthesis of aryldiazonium tetrafluoroborates, see ref 31f.
65. Hill, D. J. T.; O'Donnell, H. J.; Perera, M. C. S.; Pomery, P. J. Eur. Polym. J. 1997, 33, 1353.
66. For studies on the isomerization of azo compounds and hydrazones, see: Kuznetsov, M. A.; Suvorov, A. A. J. Org. Chem. USSR 1982, 18, 1684-1691.
67. 6.
68. For the effective carbodiazenylation of lipophilic olefins, the amount of water added to reaction mixture (method E) has to be reduced. This modification leads to prolonged reaction times of 1-2 h.
69. Hydrolytic cleavage of hydrazones to ketones: (a) Severin, T.; Poehlmann, H. Chem. Ber. 1978, 111, 1564-1577.
70. (b) Kamal, A.; Rao, M. V.; Meshram, H. M. Tetrahedron Lett. 1991, 32, 2657-2658.
71. Nasreen, A.; Adapa, S. R. Org. Prep. Proced. Int. 1999, 31, 573-576.
72. Attanasi, O.; Gasperoni, S.; Carletti, C. J. Prakt. Chem. 1980, 322, 1063-1066.
73. (e) De, S. K. Synth. Commun. 2004, 34, 4409-4416.
74. Oxidative cleavage of hydrazones: (a) Barton, D. H. R.; Jaszberenyi, J. C.; Shinada, T. Tetrahedron Lett. 1993, 34, 7191-7194.
75. (b) Barton, D. H. R.; Jaszberenyi, J. C.; Liu, W.; Shinada, T. Tetrahedron 1996, 52, 14673-14688.
76. Bhakta, C. J. Ind. Chem. Soc. 1985, 62, 380-382.
77. Chevenier, E.; Lucatelli, C.; Lucatelli, U.; Wang, W.; Gimbert, Y.; Greene, A. E. Synlett 2004, 2693-2696.
78. Strohmeier, J.; v. Angerer, E. Arch. Pharm. 1985, 318, 421-431.
79. Baccolini, G.; Dalpozzo, R.; Todesco, P. E. J. Chem. Soc., Perkin Trans. 1 1988, 971-974.
80. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, B. J. Org. Chem. 1981, 46, 3936-3938.
81. Kim, B. J.; Park, Y. S.; Beak, P. J. Org. Chem. 1999, 64, 1705-1708.
82. 3 gave 41% of 19 and 42% of recovered 6p (65% yield based on recovered starting material).