Triethylsilane-indium(III) chloride system as a radical reagent

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4981-4983

  Hayashi, Naoki ^a   Shibata, Ikuya ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; BORANE DERIVATIVE; INDIUM CHLORIDE IN 111; REAGENT; SILANE DERIVATIVE; SODIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; METALLATION;

EID: 12344288005     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047849v     Document Type: Article

References (25)

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3. For tin hydride reviews, see: (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987. (b) RajanBabu T. V. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; Wiley: New York, 1995; Vol. 7, p 5016.
4. For tin hydride reviews, see: (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987. (b) RajanBabu T. V. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; Wiley: New York, 1995; Vol. 7, p 5016.
5. 2), see: (a) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143-147. (b) Perchyonok, V. T.; Schiesser, C. H. Tetrahedron Lett. 1998, 39, 5437-5438. (c) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133-2136. (d) Ryu, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1998, 39, 6335-6336.
6. 2), see: (a) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143-147. (b) Perchyonok, V. T.; Schiesser, C. H. Tetrahedron Lett. 1998, 39, 5437-5438. (c) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133-2136. (d) Ryu, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1998, 39, 6335-6336.
7. 2), see: (a) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143-147. (b) Perchyonok, V. T.; Schiesser, C. H. Tetrahedron Lett. 1998, 39, 5437-5438. (c) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133-2136. (d) Ryu, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1998, 39, 6335-6336.
8. 2), see: (a) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143-147. (b) Perchyonok, V. T.; Schiesser, C. H. Tetrahedron Lett. 1998, 39, 5437-5438. (c) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133-2136. (d) Ryu, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1998, 39, 6335-6336.
9. 3SiH): (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194. Cyclohexadienyl-silane: (c) Studer, A.; Amrein, S. Angew. Chem., Int. Ed. 2000, 39, 3080-3082. Tri-2-furanylgermane: (d) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1999, 1415-1416. Gallium hydride: (e) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron 2003, 59, 6627-6635. Schwartz reagents: (f) Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 3137-3138.
10. 3SiH): (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194. Cyclohexadienyl-silane: (c) Studer, A.; Amrein, S. Angew. Chem., Int. Ed. 2000, 39, 3080-3082. Tri-2-furanylgermane: (d) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1999, 1415-1416. Gallium hydride: (e) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron 2003, 59, 6627-6635. Schwartz reagents: (f) Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 3137-3138.
11. 3SiH): (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194. Cyclohexadienyl-silane: (c) Studer, A.; Amrein, S. Angew. Chem., Int. Ed. 2000, 39, 3080-3082. Tri-2-furanylgermane: (d) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1999, 1415-1416. Gallium hydride: (e) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron 2003, 59, 6627-6635. Schwartz reagents: (f) Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 3137-3138.
12. 3SiH): (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194. Cyclohexadienyl-silane: (c) Studer, A.; Amrein, S. Angew. Chem., Int. Ed. 2000, 39, 3080-3082. Tri-2-furanylgermane: (d) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1999, 1415-1416. Gallium hydride: (e) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron 2003, 59, 6627-6635. Schwartz reagents: (f) Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 3137-3138.
13. 3SiH): (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194. Cyclohexadienyl-silane: (c) Studer, A.; Amrein, S. Angew. Chem., Int. Ed. 2000, 39, 3080-3082. Tri-2-furanylgermane: (d) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1999, 1415-1416. Gallium hydride: (e) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron 2003, 59, 6627-6635. Schwartz reagents: (f) Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 3137-3138.
14. 3SiH): (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194. Cyclohexadienyl-silane: (c) Studer, A.; Amrein, S. Angew. Chem., Int. Ed. 2000, 39, 3080-3082. Tri-2-furanylgermane: (d) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1999, 1415-1416. Gallium hydride: (e) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron 2003, 59, 6627-6635. Schwartz reagents: (f) Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 3137-3138.
15. We have already reported that indium hydrides act as both radical and ionic reagents in the reaction with a variety of halides, carbonyls, imines, and carbon-carbon multiple bonds. (a) Miyai, T.; Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 1998, 39, 1929-1932. (b) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. Tetrahedron Lett. 2001, 42, 4661-4663.
16. We have already reported that indium hydrides act as both radical and ionic reagents in the reaction with a variety of halides, carbonyls, imines, and carbon-carbon multiple bonds. (a) Miyai, T.; Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 1998, 39, 1929-1932. (b) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. Tetrahedron Lett. 2001, 42, 4661-4663.
17. Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J. Am. Chem. Soc. 2002, 124, 906-907.
18. Takami, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2002, 4, 2993-2995.
19. 3 system that alternatively afforded ionic reactions such as reductive aldol reaction of enones. Shibata, I.; Kato, H.; Ishida, T.; Yasuda, M.; Baba, A. Angew. Chem., Int. Ed. 2004, 43, 711-713.
20. Banfi, L.; Narisano, E.; Riva, R. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; Wiley: New York, 1995; Vol. 7, pp 4522.
21. (a) Leusink, A. J.; Budding, H. A. J. Organomet. Chem. 1968, 11, 533-539.
22. (b) Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3465-3467.
23. (c) Nakamura, E.; Machii, D.; Inubishi, T. J. Am. Chem. Soc. 1989, 111, 6849-6850.
24. 3 must be carried out below -30°C to effect hydroindation as the sole reaction.
25. 4 and concentrated. The crude mixture was purified by column chromatography to give cyclization product 8a (0.127 g, 53%).