Samarium diiodide mediated ketyl-aryl coupling reactions - Influence of substituents and trapping experiments

European Journal of Organic Chemistry

Volumn , Issue 21, 2008, Pages 3635-3646

  Wefelscheid, Ulrike K ^a   Berndt, Mathias ^a,b   Reißig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b BAYER PHARMA AG   (Germany)

Author keywords

Cyclizations; Ketyl coupling; Radical reactions; Samarium diiodide; Substituent effects

Indexed keywords

EID: 53749087530     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800293     Document Type: Article

References (100)

1. Selected reviews on samarium diiodide-mediated reactions: a) H. B. Kagan, J. L. Namy, Tetrahedron 1986, 42, 6573-6614;
2. b) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338;
3. c) F. A. Khan, R. Zimmer, J. Prakt. Chem./Chem.-Ztg. 1997, 339, 101-104;
4. d) G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321-3354;
5. e) A. Krief, A.-M. Laval, Chem. Rev. 1999, 99, 745-777;
6. f) H. B. Kagan, J. L. Namy, Top. Organomet. Chem. 1999, 2, 155-198;
7. g) P. G. Steel, J. Chem. Soc. Perkin Trans. 1 2001, 2727-2751;
8. h) A. Hölemann, Synlett 2001, 1497-1498;
9. i) H. B. Kagan, Tetrahedron 2003, 59, 10351-10372;
10. j) M. Berndt, S. Gross, A. Hölemann, H.-U. Reißig, Synlett 2004, 422-438;
11. k) D. J. Edmonds, D. Johnston, D.-J. Procter, Chem. Rev. 2004, 104, 3371-3404;
12. l) J. M. Concellón, H. Rodriguez-Solla, Chem. Soc. Rev. 2004, 33, 599-609;
13. m) D. Y. Jung, Y. H. Kim, Synlett 2005, 3019-3032.
14. For ketyl-olefin couplings see: a) G. A. Molander, C. Kenny, J. Org. Chem. 1990, 55, 6171-6176;
15. b) G. A. Molander, C. Kenny, J. Am. Chem. Soc. 1989, 111, 8236-8246;
16. c) G. A. Molander, J. A. McKie, J. Org. Chem. 1992, 57, 3132-3139;
17. d) G. A. Molander, C. Kenny, J. Org. Chem. 1994, 59, 3186-3192;
18. e) S. Fukuzawa, A. Nakanishi, T. Fujinami, S. Sakai, J. Chem. Soc. Perkin Trans. 1 1988, 1669-1675;
19. f) S. Fukuzawa, M. Iida, A. Nakanishi, T. Fujinami, S. Sakai, J. Chem. Soc., Chem. Commun. 1987, 920-921;
20. g) E. J. Enholm, A. Trivellas, Tetrahedron Lett. 1989, 30, 1063-1066;
21. h) M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shirahama, Synlett 1993, 158-162;
22. i) D. Johnston, C. F. McCuster, K. Muir, D. J. Procter, J. Chem. Soc. Perkin Trans. 1 2000, 681-695;
23. j) S. Bezzenine-Lafollée, F. Guibé, H. Villar, R. Zriba, Tetrahedron 2004, 60, 6931-6944;
24. k) F. A. Khan, R. Czerwonka, R. Zimmer, H.-U. Reißig, Synlett 1997, 995-997;
25. l) H.-U. Reißig, F. A. Khan, R. Czerwonka, C. U. Dinesh, A. L. Shaikh, R. Zimmer, Eur. J. Org. Chem. 2006, 4419-4428;
26. for ketyl-alkyne couplings see: m) A. Hölemann, H.-U. Reißig, Synlett 2004, 2732-2735;
27. for ketyl-allene couplings see: n) A. Hölemann, H.-U. Reißig, Org. Lett. 2003, 5, 1463-1466;
28. o) A. Hölemann, H.-U. Reißig, Chem. Eur. J. 2004, 10, 5493-5506;
29. p) G. A. Molander, E. P. Cormier, J. Org. Chem. 2005, 70, 2622-2626.
30. a) C. U. Dinesh, H.-U. Reißig, Angew. Chem. 1999, 111, 874-876;
31. Angew. Chem. Int. Ed. 1999, 38, 789-791;
32. b) E. Nandanan, C. U. Dinesh, H.-U. Reißig, Tetrahedron 2000, 56, 4267-4277.
33. a) H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597-2599;
34. Angew. Chem. Int. Ed. Engl. 1995, 34, 2383-2385;
35. b) H.-G. Schmalz, O. Kiehl, B. Gotov, Synlett 2002, 1253-1256.
36. a) J.-S. Shiue, C.-C. Lin, J.-M. Fang, Tetrahedron Lett. 1993, 34, 335-338;
37. b) J.-S. Shiue, C.-C. Lin, J.-M. Fang, J. Org. Chem. 1997, 62, 4643-4649;
38. c) C.-W. Kuo, J.-M. Fang, Synth. Commun. 2001, 31, 877-892.
39. a) T. Shono, N. Kise, T. Suzumoto, T. Morimoto, J. Am. Chem. Soc. 1986, 108, 4676-4677;
40. b) N. Kise, T. Suzumoto, T. Shono, J. Org. Chem. 1994, 59, 1407-1413.
41. a) R. Gorny, H. J. Schäfer, R. Fröhlich, Angew. Chem. 1995, 107, 2188-2191;
42. Angew. Chem. Int. Ed. Engl. 1995, 34, 2007-2009;
43. b) J. Heinemann, H. J. Schäfer, R. Fröhlich, B. Wibbeling, Eur. J. Org. Chem. 2003, 2919-2932.
44. Reviews dealing with synthetic applications of dearomatizing processes: a) for reductive dearomatizations see: L. N. Mander, Synlett 1991, 134-144;
45. T. J. Donohoe, R. Garg, C. A. Stevenson, Tetrahedron: Asymmetry 1996, 7, 317-344;
46. A. Schultz, Chem. Commun. 1999, 1263-1271;
47. b) for nucleophilic dearomatizations see: F. L. Ortiz, M. J. Iglesias, I. Fernández, C. M. A. Sánchez, G. R. Gómez, Chem. Rev. 2007, 107, 1580-1691;
48. c) for transition metal mediated dearomatizations see: A. R. Pape, K. P. Kaliappan, E. P. Kündig, Chem. Rev. 2000, 100, 2917-2940;
49. d) for oxidative dearomatizations see: S. Quideau, L. Pouységu, D. Deffieux, Synlett 2008, 467-495; and references in these reviews.
50. a) Preliminary study of substituent effects and trapping experiments: M. Berndt, H.-U. Reißig, Synlett 2001, 1290-1292;
51. b) S. Gross, H.-U. Reißig, Synlett 2002, 2027-2030;
52. c) R. Senthil Kumaran, H.-U. Reißig, Synlett 2008, 991-994;
53. [1j] [10] a) M. Berndt, I. Hlobilová, H.-U. Reißig, Org. Lett. 2004, 6, 957-960;
54. b) F. Aulenta, M. Berndt, I. Brüdgam, H. Hartl, S. Sörgel, H.-U. Reißig, Chem. Eur. J. 2007, 13, 6047-6062;
55. c) U. K. Wefelscheid, H.-U. Reißig, Adv. Synth. Catal. 2008, 350, 65-69.
56. a) S. Gross, H.-U. Reißig, Org. Lett. 2003, 5, 4305-4307;
57. b) V. Blot, H.-U. Reißig, Eur. J. Org. Chem. 2006, 4989-4992.
58. [11];
59. b) V. Blot, H.-U. Reißig, Synlett 2006, 2763-2766.
60. F. Aulenta, U. K. Wefelscheid, I. Brüdgam, H.-U. Reißig, Eur. J. Org. Chem. 2008, 2325-2335.
61. Review: P. W. Rabideau, Z. Marcinow, Org. React. 1992, 42, 1-334.
62. For A-values see: a) J. A. Hirsch, Top. Stereochem. 1967, 1, 199-222;
63. b) N. L. Allinger, L. A. Freiberg, J. Org. Chem. 1966, 31, 894-897.
64. M. Berndt, Dissertation, Freie Universität Berlin 2003.
65. a) E. C. Taylor, Y. Wang, Heterocycles 1998, 48, 1537-1553;
66. b) for similar conditions with less catalyst loading see: R. C. Larock, W.-Y. Leung, S. Stolz-Dunn, Tetrahedron Lett. 1989, 30, 6629-6632.
67. a) T. Jeffery, Tetrahedron Lett. 1991, 32, 2121-2124;
68. b) A. Padwa, A. Zanka, M. P. Cassisdy, J. M. Harris, Tetrahedron 2003, 59, 4939-4944.
69. U. K. Wefelscheid, Dissertation, Freie Universität Berlin, 2007.
70. [25]).
71. The use of HMPA raises the reducing potential of samarium diiodide and is required for many ketyl coupling reactions. See: a) K. Otsubo, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 5763-5764;
72. b) J. Inanaga, M. Ishikawa, M. Yamaguchi, Chem. Lett. 1987, 1485-1486;
73. c) M. Shabangi, R. A. Flowers II, Tetrahedron Lett. 1997, 38, 1137-1140;
74. d) J. B. Shotwell, J. M. Sealy, R. A. Flowers II, J. Org. Chem. 1999, 64, 5251-5255;
75. e) R. S. Miller, J. M. Sealy, M. Shabangi, M. L. Kuhlman, J. Fuchs, R. A. Flowers II, J. Am. Chem. Soc. 2000, 122, 7718-7722;
76. f) E. Prasad, R. A. Flowers II, J. Am. Chem. Soc. 2002, 124, 6895-6899;
77. g) R. A. Flowers II, X. Xu, C. Timmons, G. Li, Eur. J. Org. Chem. 2004, 2988-2990;
78. h) A. Dahlén, G. Hilmersson, Eur. J. Inorg. Chem. 2004, 3393-3404;
79. recent review: R. A. Flowers II, Synlett, in press. There has been no general success by replacing HMPA with less toxic cosolvents.
80. This is a widely used procedure for the preparation of samarium diiodide which was first employed by Kagan: J. L. Namy, P. Girard, H. Kagan, New J. Chem. 1977, 1, 5-7.
81. 2. We thank Professor H. Yamamoto for discussions on this problem and suggesting this pathway.
82. a) H. Ohno, S.-i. Maeda, M. Okumura, R. Wakayama, T. Tanaka, Chem. Commun. 2002, 316-317;
83. b) H. Ohno, M. Okumura, S.-i. Maeda, H. Iwasaki, R. Wakayama, T. Tanaka, J. Org. Chem. 2003, 68, 7722-7732.
84. T. Linker, M. Schmittel, Radikale und Radikalionen in der Organischen Synthese, Wiley-VCH, Weinheim 1998.
85. Model DFT calculations performed by Prof. T. Strassner, Technische Universität Dresden, could not include samarium. Therefore, these calculations did not provide conclusive evidence for the mechanism involved.
86. For radical stabilities see: H. Zipse, Top. Curr. Chem. 2006, 263, 163-189.
87. For these substrates we can not rigorously exclude a different mechanism. Transfer of two electrons to the aromatic ring may provide a dianion which immediately adds to the carbonyl group. However, we assume it unlikely that the two-electron transfer is feasible. Furthermore, the stereoselectivity which is in all cases indentical makes a switch in the mechanism also unlikely.
88. H. Ohno, R. Wakayama, S.-i. Maeda, H. Iwasaki, M. Okumura, C. Iwata, H. Mikamiyama, T. Tanaka, J. Org. Chem. 2003, 68, 5909-5916.
89. O. Rademacher, M. Berndt, H.-U. Reißig, Z. Kristallogr. - New Cryst. Struct. 2001, 216, 593-594.
90. For a theoretical study of related electrochemical couplings strongly supporting involvement of ketyls, see: N. Kise, J. Org. Chem. 2004, 69, 2147-2152.
91. For selected examples of synthesis and reactivity of compounds with cyclohexa-1,4-diene substructure, see: a) P. A. Wender, T. E. Jenkins, J. Am. Chem. Soc. 1989, 111, 6432-6434;
92. b) T. Linker, L. Fröhlich, J. Am. Chem. Soc. 1995, 117, 2694-2697;
93. c) F. Alonso, M. Yus, Recent Res. Devel. Org. Chem. 1999, 3, 9-59;
94. d) G. Hilt, S. Lüers, K. Polborn, Isr. J. Chem. 2001, 41, 317-327;
95. e) G. Hilt, K. I. Smolko, Angew. Chem. 2003, 115, 2901-2903;
96. Angew. Chem. Int. Ed. 2003, 42, 2795-2797;
97. f) G. Hilt, W. Hess, K. Harms, Org. Lett. 2006, 8, 3287-3290;
98. g) A. Fürstner, C. C. Stimson, Angew. Chem. 2007, 119, 9001-9005;
99. Angew. Chem. Int. Ed. 2007, 46, 8845-8849.
100. K. Hattori, H. Sajiki, K. Hirota, Tetrahedron 2001, 57, 4817-4824.