Allylation and vinylation of aryl radicals generated from diazonium salts

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9609-9616

  Heinrich, Markus R ^a   Blank, Olga ^a   Ullrich, Daniela ^a   Kirschstein, Marcel ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; CHLORINATION; STYRENE; SUBSTRATES;

ALLYLATION; ARYL RADICALS; DIAZONIUM SALTS; VINYLATION;

SALTS;

DIAZONIUM COMPOUND; RADICAL;

ALLYLATION; ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; PHASE TRANSITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; VINYLATION;

EID: 36849084048     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701717k     Document Type: Article

References (100)

1. Lewis, S. N.; Miller, J. J.; Winstein, S. J. Org. Chem. 1972, 37, 1478-1484.
2. For reviews on allylations and vinylations, see: (a) Ramaiah, M. Tetrahedron 1987, 43, 3541-3676.
3. (b) Curran, D. P. Synthesis 1988, 417-439.
4. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286.
5. (a) Kosugi, M.; Kurino, K.; Takayama, K.; Migita, T. J. Organomet. Chem. 1973, 56, C11-C13.
6. (b) Grignon, J.; Pereyre, M. J. Organomet. Chem. 1973, 61, C33-C35.
7. (c) Grignon, J.; Servens, C.; Pereyre, M. J. Organomet. Chem. 1975, 96, 225-235.
8. For examples demonstrating the versatility of allyltin-based reactions, see: (a) Keck, G. E.; Yates, J. B. J. Am. Chem. Soc 1982, 104, 5829-5831.
9. (b) Keck, G. E.; Enholm, E. J.; Kachensky, D. F. Tetrahedron Lett. 1984, 25, 1867-1870.
10. (c) Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron 1985, 41, 4079-4094.
11. (d) Keck, G. E.; Kachensky, D. F.; Enholm, E. J. J. Org. Chem. 1985, 50, 4317-4325.
12. (e) Sibi, M. P.; Chandramouli, S. V. Tetrahedron Lett. 1997, 38, 8929-8932.
13. (f) Sibi, M.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163-171.
14. For an overview, see: Rosenstein, I. J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 50-71.
15. (a) Keck, G. E.; Byers, H. J. J. Org. Chem. 1985, 50, 5442-5444.
16. (b) Yanagisawa, A.; Noritake, Y.; Yamamoto, H. Chem. Lett. 1988, 1899-1902.
17. (c) Breuilles, P.; Uguen, D. Tetrahedron Lett. 1990, 31, 357-360.
18. Barton, D. H. R.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1986, 1613-1619.
19. (a) Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210.
20. (b) Le Guyader, F.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. J. Am. Chem. Soc. 1997, 119, 7410-7411.
21. (c) Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem., Int. Ed. 1998, 37, 2864-2866.
22. (d) Blakskjaer, P.; Pedersen, L.; Skrydstrup, T. J. Chem. Soc., Perkin Trans. 1 2001, 910-916.
23. Johnson, M. D. Acc. Chem. Res. 1983, 16, 343-349.
24. For radical additions to silanes with subsequent fluoride-induced elimination, see: (a) Porter, N. A.; Zhang, G.; Reed, A. D. Tetrahedron Lett. 2000, 41, 5773-5777.
25. (b) Chabaud, L.; Landais, Y.; Renaud, P. Org. Lett. 2002, 4, 4257-4280.
26. (c) Briggs, M. E.; Zard, S. Z. Synlett 2005, 334-336.
27. Huval, C. D.; Singleton, D. A. Tetrahedron Lett. 1993, 34, 3041-3042.
28. Ouvry, G.; Quiclet-Sire, B.; Zard, S. Z. Angew. Chem., Int. Ed. 2006, 45, 5002-5006.
29. For overviews, see: (a) Curran, D. P.; Porter, N. A.; Giese, B., Eds. Stereochemistry of Radical Reactions; Concepts, Guidelines, and Synthetic Applications; VCH: Weinheim, Germany, 1996.
30. (b) Giese, B. Radicals in Organic Synthesis; Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
31. For the first report on allylations of aryl radicals, see: Al Adel, I.; Salami, B. A.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 934-938.
32. For other studies on allylations of aryl radicals, see: (a) Doyle, M. P.; Siegfried, B.; Elliot, R. C.; Dellaria, J. F., Jr. J. Org. Chem. 1977, 42, 2431-2436.
33. (b) Migita, T.; Kosugi, M.; Takayama, K.; Nakagawa, Y. Tetrahedron 1973, 29, 51-55.
34. (c) Migita, T.; Nagai, K.; Kosugi, M. Bull. Chem. Soc. Jpn. 1983, 56, 2480-2484.
35. (d) Yashkina, L. V.; Kopylova, B. V. Bull. Acad. Sci. USSR, Chem. Sci. 1989, 38, 863-865.
36. Ek, F.; Axelsson, O.; Wistrand, L.-G.; Frejd, T. J. Org. Chem. 2002, 67, 6376-6381.
37. (a) Cohen, S. G.; Wolosinski, H. T.; Scheuer, P. J. J. Am. Chem. Soc. 1950, 72, 3952-3953.
38. (b) Reijnhart, A. F. A. Recl. Trav. Chim. Pays-Bas 1927, 46, 72-76.
39. Rondestvedt, C. S. Org. React. 1976, 24, 225-259.
40. For Meerwein arylations of (nonacceptor substituted) 1,3-butadienes, see: (a) Taylor, E. C; Strojny, E. J. J. Am. Chem. Soc. 1956, 78, 5104-5108.
41. (b) Arai, E.; Tokuyama, H.; Linsell, M. S.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 71-74.
42. For notable exceptions, see: (a) Raucher, S.; Koolpe, G. A. J. Org. Chem. 1983, 48, 2066-2069.
43. (b) Gorbovoi, P. M.; Kudrik, E. Y.; Grishchuk, B. D. Russ. J. Gen. Chem. 1998, 68, 1132-1134.
44. (c) Molinaro, C.; Mowat, J.; Gosselin, F.; O'Shea, P. D.; Marcoux, J.-F.; Angelaud, R.; Davies, I. W. J. Org. Chem. 2007, 72, 1856-1858.
45. (d) Reference 16.
46. (a) Galli, C. Chem. Rev. 1988, 88, 765-792.
47. (b) Citterio, A.; Minisci, F.; Vismara, E. J. Org. Chem. 1982, 47, 81-88.
48. (c) Garden, S. J.; Avila, D. V.; Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U.; Lusztyk, J. J. Org. Chem. 1996, 61, 805-809.
49. (a) Heinrich, M. R.; Blank, O.; Wölfel, S. Org. Lett. 2006, 8, 3323-3325.
50. (b) Heinrich, M. R.; Blank, O.; Wetzel, A. J. Org. Chem. 2007, 72, 476-484.
51. (c) Heinrich, M. R.; Wetzel, A.; Kirschstein, M. Org. Lett. 2007, 9, 3833-3835.
52. Depending on whether the aryl radicals are trapped by the diazonium salts before or after reacting with the olefin (as alkyl radicals), biaryl azo compounds or carbodiazenylation products are obtained. See also ref 22.
53. For relative rate constants of β-fragmentations, see: Wagner, P. J.; Sedon, J. H.; Lindstrom, M. J. J. Am. Chem. Soc. 1978, 100, 2579-2580.
54. A reliable determination of the degree of hydrogen abstraction by p-fluoroaryl radicals was not possible due to the volatility of fluorobenzene.
55. -1), see ref 21c. For relative rates of aryl radical additions to various olefins, see: Bridger, R. F.; Russell, G. A. J. Am. Chem. Soc. 1963, 85, 3754-3765.
56. Giese, B. Angew. Chem., Int. Ed. 1983, 22, 753-764.
57. Attempts to achieve vinylation with tetrachloroemene and diazonium salt 1a gave nearly quantitative yields of anisole and only traces of trichlorostyrene although additions of aryl radicals to this substrate have been reported. See ref 17.
58. For intramolecular additions of alkyl radicals to nitrobenzenes, see: Beckwith, A. L. J.; Lawton, D. L. J. Chem. Soc., Perkin Trans. 2 1973, 2134-2137.
59. The allylation reported by Freyd does tolerate o-nitro substituents due to the use of allyl bromide, which undergoes faster fragmenation. See ref 16.
60. The structure of nitro compound 4d was confirmed by conversion to aminothiazole 5 according to the literature: Hardy, K. D.; Harrington, F. P.; Stachulski, A. V. J. Chem. Soc., Perkin Trans. 1 1984, 1227-1236.
61. (a) Hanzawa, Y.; Kowase, N.; Taguchi, T. Tetrahedron Lett. 1998, 39, 583-586.
62. (b) Perri, S. T.; Dyke, H. J.; Moore, H. W. J. Org. Chem. 1989, 54, 2032-2034.
63. (c) Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 112, 1897-1905.
64. (d) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
65. (e) Ogawa, T.; Kusume, K.; Tanaka, M.; Hayami, K.; Suzuki, H. Synth. Commun. 1989, 19, 2199-2207.
66. (f) Reginato, G.; Gaggini, F.; Mordini, A.; Valacchi, M. Tetrahedron 2005, 61, 6791-6800.
67. (g) Sahli, S.; Stump, B.; Welti, T.; Schweizer, W. B.; Diederich, F.; Blum-Kaelin, D.; Aebi, J. D.; Boehm, H.-J. Helv. Chim. Acta 2005, 88, 707-730.
68. (a) Akiyama, S.; Nakatsuji, S.; Yoshida, K.; Nakashima, K.; Hagiwara, T.; Tsuruta, H.; Yoshida, T. Bull. Chem. Soc. Jpn. 1983, 56, 361-362.
69. (b) Cunico, R. F.; Maity, B. C. Org. Lett. 2003, 5, 4947-4950.
70. (c) Rodriguez, G. J.; Tejedor, L. J.; Rumbero, A.; Canoira, L. Tetrahedron 2006, 62, 3075-3080.
71. (d) Mitsudo, T.; Takagi, M.; Zhang, S.-W.; Watanabe, Y. J. Organomet. Chem. 1992, 423, 405-414.
72. (e) Organ, M. G.; Cooper, J. T.; Rogers, L. R.; Soleymanzadeh, F.; Payl, T. J. Org. Chem. 2000, 65, 7959-7970.
73. (a) Carran, J.; Waschbuesch, R.; Marinetti, A.; Savignac, P. Synthesis 1996, 1494-1498.
74. (b) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095-4101.
75. (c) Lin, S.-T.; Lee, C.-C.; Liang, D. W. Tetrahedron 2000, 56, 9619-9624.
76. (d) Shono, T.; Ito, K.; Tsubouchi, A.; Takeda, T. Org. Biomol. Chem. 2005, 3, 2914-2916.
77. (e) Minato, A.; Suzuki, K.; Tamao, K. J. Am. Chem. Soc. 1987, 109, 1257-1258.
78. (f) Negishi, E.-I.; Shi, J.-C.; Zeng, X. Tetrahedron 2005, 61, 9886-9895.
79. (g) Tan, Z.; Negishi, E.-I. Angew. Chem., Int. Ed. 2006, 45, 762-765.
80. (h) Shi, J.; Zeng, X.; Negishi, E.-I. Org. Lett. 2003, 5, 1825-1828.
81. (a) Gruner, M.; Pfeifer, D.; Becker, H. G. O.; Radeglia, R.; Epperlein, J. J. Prakt. Chem. 1985, 327, 63-79.
82. (b) Bahr, J. L.; Yang, J.; Kosynkin, D. V.; Bronikowski, M. J.; Smalley, R. E.; Tour, J. M. J. Am. Chem. Soc. 2001, 123, 6536-6542.
83. (c) Časar, Z.; Leban, I.; Majcen-LeMaréchal, A.; Lorcy, D. J. Chem. Soc., Perkin Trans. 1 2002, 1568-1573.
84. (d) Huang, H.; Liu, X.; Deng, J.; Zheng, Z. Org. Lett. 2006, 8, 3359-3362.
85. (e) Young, W. G.; Caserio, F. F.; Brandon, D. D., Jr. J. Am. Chem. Soc. 1960, 82, 6163-6168.
86. (f) Ma, S.; Lu, X.; Li, Z. J. Org. Chem. 1992, 57, 709-713.
87. (a) Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333-4339.
88. (b) Olah, G. A.; Krishnamurthy, V. V.; Singh, B. P.; Iyer, P. S. J. Org. Chem. 1983, 48, 955-963.
89. (c) Lajis, N. H.; Khan, M. N. Tetrahedron 1992, 48, 1109-1114.
90. (d) Hanzawa, Y.; Kowase, N.; Momose, S.; Taguchi, T. Tetrahedron 1998, 54, 11387-11398.
91. (e) Stuedemann, T.; Gupta, V.; Engman, L.; Knochel, P. Tetrahedron Lett. 1997, 38, 1005-1008.
92. (f) Krasovsky, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 6040-6044.
93. (g) Villieras, J.; Rambaud, M. Synthesis 1982, 924-926.
94. Nakamura, H.; Kamakura, T.; Onagi, S. Org. Lett. 2006, 8, 2095-2098.
95. (a) Barluenga, J.; Moriel, P.; Aznar, F.; Valdés, C. Adv. Synth. Catal. 2006, 348, 347-353.
96. (b) Braverman, S.; Zafrani, Y. Tetrahedron 1998, 54, 1901-1912.
97. (c) Mun, S.; Lee, J.-E.; Yun, J. Org. Lett. 2006, 8, 4887-4889.
98. (a) Okada, Y.; Yokozawa, M.; Akiba, M.; Oishi, K.; Okawa, K.; Akeboshi, T.; Kawamura, Y.; Inokuma, S.; Nakamura, Y.; Nishimura, J. Org. Biomol. Chem. 2003, 1, 2506-2511.
99. (b) Moore, J. A.; Ahlstrom, D. H. J. Org. Chem. 1961, 26, 5254-5255.
100. (c) Khartulyari, A. S.; Kapur, M.; Maier, M. E. Org. Lett. 2006, 8, 5833-5836.