Preparations and reactions of functionalized silyllithiums

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 5, 1997, Pages 945-955

  Kawachi, Atsushi ^a   Tamao, Kohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONALIZED; HIGH STABILITY; WITTIG REARRANGEMENT;

LITHIUM; STABILITY;

CATALYST ACTIVITY;

EID: 0011486295     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.70.945     Document Type: Article

References (102)

1. "Comprehensive Carbanion Chemistry", ed by E. Buncel and T. Durst, Elsevier, Amsterdam, Part A (1980) and Part B (1984);
2. B. J. Wakefield, "Organolithium Methods", Academic Press, London (1988);
3. P. G. Williard, "Comprehensive Organic Synthesis", ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, pp. 1-47.
4. P. Beak, W. J. Zajdel, and D. B. Reitz, Chem. Rev., 84, 471 (1984);
5. G. Boche, Angew. Chem., Int. Ed. Engl, 28, 277 (1989); α-Aminoorganolithiums:
6. I. Coldham, R. Hufton, and D. J. Snowden, J. Am. Chem. Soc, 118, 5322 (1996).
7. Reviews: a) G. Köbrich, Angew. Chem., Int. Ed. Engl, 11, 473 (1972);
8. A. Maercker, Angew. Chem., Int. Ed. Engl, 32, 1023 (1993); α-Alkoxyorganolithiums:
9. G. Boche, F. Bosold, J. C. W. Lohrenz, A. Opel, and P. Zulauf, Chem. Ben, 126, 1873 (1993); α-Chloroorganolithiums:
10. D. Seebach, H. Siegel, J. Gabriel, and R. Hassig, Helv. Chim. Acta, 63, 2046 (1980);
11. A. Müller, M. Marsch, K. Harms, J. C. W. Lohrenz, and G. Boche, Angew. Chem., Int. Ed. Engl, 35, 1518 (1996).
12. Reviews: a) I. Fleming, "Comprehensive Organic Chemistry", ed by E. Barton and W. D. Ollis, Pergamon Press, Oxford (1979), Vol. 3, pp. 664-669;
13. M. Fujita and T. Hiyama, J. Synth. Org. Chem. Jpn., 42, 293 (1984);
14. J. B. Lambert and W. J. Schulz, Jr., "The Chemistry of Organic Silicon Compounds", ed by S. Patai and Z. Rappoport, Wiley, Chichester (1989), pp. 1007-1010;
15. K. Tamao and A. Kawachi, Adv. Organomet. Chem., 38, 1 (1995);
16. P. D. Lickiss and C. M. Smith, Coord. Chem. Rev., 145, 75 (1995).
17. H. Gilman and G. D. Lichtenwalter, J. Am. Chem. Soc, 80, 608 (1958).
18. M=Na: H. Sakurai, A. Okada, M. Kira, and K. Yonezawa, Tetrahedron Lett., 12, 1511 (1971);
19. M=Li: W. C. Still, J. Org. Chem., 41, 3063 (1976);
20. M=K: R. J. P. Corriu, C. Guerin, and B. Kolani, Bull Soc. Chim. Fr., 1985, 974.
21. S. Nozakura and S. Konotsune, Bull Chem. Soc. Jpn., 29, 322 (1956);
22. R. A. Benkeser, Acc. Chem. Res., 4, 94 (1971);
23. C. S. Li, D. F. Ehler, and R. A. Benkeser, Org. Synth., Coll. Vol. 6, 747 (1988);
24. K. Naumann, G. Zon, and K. Mislow, J. Am. Chem. Soc, 91, 7012 (1969).
25. H. Watanabe, K. Higuchi, Y. Goto, T. Muraoka, J. Inose, M. Kageyama, Y. Iizuka, M. Nozaki, and Y. Nagai, J. Organomet. Chem., 218, 27 (1981).
26. H. Gilman and W. Steudel, Chem. Ind. (London), 1959, 1094.
27. D. M. Roddick, R. H. Heyn, and T. D. Tilley, Organometallics, 8, 324 (1989).
28. J. Ohshita, Y. Masaka, S. Masaoka, M. Ishikawa, A. Tachibana, T. Yano, and T. Yamabe, J. Organomet. Chem., 473, 15 (1994);
29. J. Ohshita, Y. Masaka, S. Masaoka, M. Ishikawa, A. Tachibana, T. Yano, and T. Yamabe, Organometallics, 15, 3136 (1996).
30. A. C. Hopkinson and M. H. Lien, Tetrahedron, 37, 1105 (1981);
31. E. Magnusson, Tetrahedron, 41, 2945 (1985).
32. R. West, J. Organomet. Chem., 300, 327 (1986);
33. C. L. Smith and R. Gooden, J. Organomet. Chem., 81, 33 (1974);
34. R. Boudjouk, U. Samaraweera, R. Sooriyakumaran, J. Chrusciel, and K. R. Anderson, Angew. Chem., Int. Ed. Engl, 27, 1355 (1988);
35. T. Tsumuraya, S. A. Batcheller, and S. Masamune, Angew. Chem., Int. Ed. Engl, 30, 902 (1991);
36. R. J. P. Corriu, G. Lanneau, C. Priou, F. Soulairol, N. Auner, R. Probst, R. Conlin, and C. J. Tan, J. Organomet. Chem., 466, 55 (1994).
37. Reviews: a) J. A. Marshall, "Comprehensive Organic Synthesis", ed by B. M. Trost, I. Fleming, and G. Pattenden, Pergamon Press, Oxford (1991), Vol. 3, pp. 975-1014;
38. T. Nakai and K. Mikami, Chem. Rev., 86, 885 (1986);
39. R. W. Hoffmann, Angew. Chem., Int. Ed. Engl, 18, 563 (1979).
40. B. H. Lipshutz, D. C. Reuter, and E. L. Ellsworth, J. Org. Chem., 54, 4975 (1989).
41. K. Tamao, A. Kawachi, and Y. Ito, J. Am. Chem. Soc, 114, 3989 (1992).
42. K. Tamao and A. Kawachi, Angew. Chem., Int. Ed. Engl, 34, 818 (1995).
43. K. Tamao and A. Kawachi, Organometallics, 14, 3108 (1995).
44. For LDMAN: T. Cohen, J. P. Sherbine, J. R. Matz, R. R. Hutchins, B. M. McHenry, and P. R. Willey, J. Am. Chem. Soc, 106, 3245 (1984);
45. For LDBB: P. K. Freeman and L. L. Hutchinson, J. Org. Chem., 45, 1924 (1980).
46. A stannylsodium was obtained by reduction of a stannyl chloride with sodium naphthalenide: J. C. Podestá, N. N. Giagante, A. E. Zuñiga, G. O. Danelon, and O. A. Mascaretti, J. Org. Chem., 59, 3747 (1994).
47. K. Tamao, A. Kawachi, and Y. Ito, Organometallics, 12, 580 (1993).
48. K. Tamao, G.-R. Sun, A. Kawachi, and S. Yamaguchi, Organometallics, 16, 780 (1997).
49. 29Si shift of the silyllithium 1 was reported uncorrectly in the original paper (Ref. 16) and reinvestigated in 1994.
50. A. Kawachi and K. Tamao, Organometallics, 15, 4653 (1996).
51. G. A. Olah and R. Hunadi, J. Am. Chem. Soc, 102, 6989 (1980);
52. E. Buncel, T. K. Venkatachalan, B. Eliasson, and U. Edlund, J. Am. Chem. Soc, 107, 303 (1985);
53. U. Edlund, T. Lejon, T. K. Venkatachalam, and E. Buncel, J. Am. Chem. Soc, 107, 6408 (1985).
54. K. Tamao, A. Okamoto, T. Kobayashi, A. Kawachi, and Y. Ito, unpublished results.
55. Recent works on preparation of oligosilanyllithiums and oligosilanes: a) A. Sekiguchi, M. Nanjo, C. Kabuto, and H. Sakurai, J. Am. Chem. Soc, 117, 4195 (1995);
56. A. Sekiguchi, M. Nanjo, C. Kabuto, and H. Sakurai, Organometallics, 14, 2630 (1995).
57. Y. Apeloig, "The Chemistry of Organic Silicon Compounds", ed by S. Patai and Z. Rappoport, Wiley, Chichester (1989), pp. 655-761.
58. A. Kawachi and K. Tamao, unpublished results; The term "silyl (alkyl) magnesium" does not represent the "real" structure, but is used for species consisting of a 1:1 mixture of silyllithium and alkylmagnesium halide.
59. H. Hayami, M. Sato, S. Kanemoto, Y. Morizawa, K. Oshima, and H. Nozaki, J. Am. Chem. Soc, 105, 4491 (1983).
60. T. Clark and P. v. R. Schleyer, J. Organomet. Chem., 191, 347 (1980).
61. In carbenoid chemistry, ionization of this type is sometimes called "metal-assisted ionization" which involves a definite heteroatom-metal interaction, see: M. Topolski, M. Duraisamy, J. Rachon, J. Gawronski, K. Awronska, V. Goedken, and H. M. Walborsky, J. Org. Chem., 58, 546 (1993).
62. For an example of successive introduction of a nucleophile and an electrophile to carbenoids in organic synthesis, see: P. Knochel, N. Jeong, M. J. Rozema, and M. C. P. Yeh, J. Am. Chem. Soc, 111, 6474 (1989).
63. Recent reports on Wittig rearrangement: a) K. Tomooka, P.-H. Keong, and T. Nakai, Tetrahedron Lett., 36, 2789 (1995);
64. A. R. Katritzky, H. Wu, and L. Xie, J. Org. Chem., 61, 4035 (1996).
65. Aza-Wittig rearrangement: a) T. Durst, R. V. D. Elzen, and M. LeBelle, J. Am. Chem. Soc, 94, 9261 (1972);
66. C. Broka and T. Shen, J. Am. Chem. Soc, 111, 2981 (1989);
67. I. Coldham, J. Chem. Soc, Perkin Trans. I, 1993, 1275;
68. J. Ahman and P. Somfai, J. Am. Chem. Soc, 116, 9781 (1994);
69. J. Ahman and P. Somfai, Tetrahedron Lett., 36, 303 (1995);
70. J. C. Anderson, D. C. Siddons, S. C. Smith, and M. E. Swarbrick, J. Chem. Soc, Chem. Commun., 1995, 1835;
71. I. Coldham, A. J. Collis, R. J. Mould, and R. E. Rathmell, J. Chem. Soc, Perkin Trans. I, 1995, 2739;
72. R. E. Gawley, Q. Zhang, and S. Campagna, J. Am. Chem. Soc, 117, 11817 (1995);
73. J. Anderson, D. C. Siddons, S. C. Smith, and M. E. Swarbrick, J. Org. Chem., 61, 4820 (1996).
74. For a review on rearrangements involving silicon, see: a) A. G. Brook and A. R. Bassindale, "Rearrangements in Ground and Excited States", ed by P. de Mayo, Academic Press, New York (1980), pp. 149-227; The term sila-Wittig rearrangement is used to differentiate the present reaction from the silyl-Wittig rearrangement (reversed Brook rearrangement):
75. A. Wright and R. West, J. Am. Chem. Soc, 96, 3214, 3222, and 3227 (1974).
76. A. Kawachi, N. Doi, and K. Tamao, J. Am. Chem. Soc, 119, 233 (1997).
77. A similar solvent effect has been well documented in the Wittig rearrangements of carbanions. a) G. Wittig and E. Stahnecker, Justus Liebigs Ann. Chem., 605, 69 (1957);
78. K. Mikami, T. Kasuga, K. Fujimoto, and T. Nakai, Tetrahedron Lett, 26, 4185 (1986). See also Ref. 35i.
79. W. C. Still and A. Mitra, J. Am. Chem. Soc, 100, 1927 (1978);
80. Y.-D. Wu, K. N. Houk, and A. Marshall, J. Org. Chem., 55, 1421 (1990);
81. R. Hoffmann and R. Brückner, Angew. Chem., Int. Ed. Engl, 31, 647 (1992);
82. E. J. Verner and T. Cohen, J. Am. Chem. Soc, 114, 375 (1992);
83. K. Mikami, T. Uchida, T. Hirano, Y.-D. Wu, and K. N. Houk, Tetrahedron, 50, 5917 (1994).
84. The term "tertiary allyl" means that the allylic carbon is tertiary. The terms primary and secondary are used in a similar way in this paper.
85. A. Kawachi, N. Doi, and K. Tamao, unpublished results.
86. K. Tamao, N. Ishida, T. Tanaka, and M. Kumada, Organometallics, 2, 1694 (1983);
87. I. Fleming, Chemtracts, Org. Chem., 9, 1 (1996);
88. G. Jones and Y. Landais, Tetrahedron, 37, 7599 (1996);
89. K. Tamao, "Advances in Silicon Chemistry", ed by G. Larson, JAI Press, Greenwich, Connecticut (1996), Vol. 3, pp. 1-62.
90. For examples; a) R. A. N. C. Crump, I. Fleming, J. H. M. Hill, D. Parker, N. L. Reddy, and D. Waterson, J. Chem. Soc, Perkin Trans. 1, 1992, 3277;
91. I. Fleming, Pure Appl Chem., 60, 71 (1988), and references cited therein.
92. I. Fleming, J. Dunogues, and R. Smithers, Org. React., 37, 57 (1989);
93. S. S. Magar and P. L. Fuchs, Tetrahedron Lett., 32, 7513 (1991).
94. D. J. Ager, Org. React., 38, 1 (1990).
95. Recently, Fleming et al. have found another solution to this problem by use of a well-designed (allylsilyl) lithium: An allyl group, 2-methyl-2-butenyl group, on the silicon can be removed selectively with very weak acids with other allyl-, vinyl-, and β-hydroxy-silane moieties intact. I. Fleming and S. B. D. Winter, Tetrahedron Lett., 34, 7287 (1993).
96. K. Tamao, A. Kawachi, Y. Tanaka, H. Ohtani, and Y. Ito, Tetrahedron, 52, 5765 (1996).
97. I. Fleming and T. W. Newton, J. Chem. Soc., Perkin Trans. 7, 1984, 1805;
98. I. Fleming and A. P. Thomas, J. Chem. Soc, Chem. Commun., 1986, 1456.
99. J. A. Marshall, Chem: Rev., 89, 1503 (1989), and references cited therein.
100. I. Fleming, T. W. Newton, and F. Roessler, J. Chem. Soc, Perkin Trans. 1, 1981, 2527.
101. 52) A. Kawachi, M. Shiro, and K. Tamao, unpublished results (1997).
102. H. V. R. Davis, M. M. Olmstead, K. Ruhlandt-Senge, and P. P. Power, J. Organomet. Chem., 462, 1 (1993).