Lewis acid-catalyzed trans-carbosilylation of simple alkynes

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 4874-4875

  Asao, Naoki ^a,b   Yoshikawa, Eiji ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000895179     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960779o     Document Type: Article

References (25)

1. Ziegler, K.; Bähr, K. Chem. Ber. 1928, 61, 253.
2. For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn, and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
3. For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn, and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
4. For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn, and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
5. For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn, and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
6. For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn, and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
7. For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, B, Al, and Cu compounds). (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn, and catalytic Ni, Pd, Pt compounds). (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333 (organo-Al/Ti and Al/Zr system). (d) Knochel, P. Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd, Ni, Mn compounds). (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, Al compounds).
8. The net carbosilylation from the three-component coupling reaction was reported.
9. (a) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778.
10. (b) Obora, Y.; Tsuji, Y.; Kawamura, T. J. Am. Chem. Soc. 1995, 117, 9814.
11. For direct C-Si bond cleavages within a transition metal coordination sphere, see: (a) Lin, W.; Wilson, S. R.; Girolami, G. S. J. Am. Chem. Soc. 1993, 115, 3022. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 1193. (c) Chang, L. S.; Johnson, M. P.; Fink, M. J. Organometallics 1991, 10, 1219 and references cited therein.
12. For direct C-Si bond cleavages within a transition metal coordination sphere, see: (a) Lin, W.; Wilson, S. R.; Girolami, G. S. J. Am. Chem. Soc. 1993, 115, 3022. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 1193. (c) Chang, L. S.; Johnson, M. P.; Fink, M. J. Organometallics 1991, 10, 1219 and references cited therein.
13. For direct C-Si bond cleavages within a transition metal coordination sphere, see: (a) Lin, W.; Wilson, S. R.; Girolami, G. S. J. Am. Chem. Soc. 1993, 115, 3022. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 1193. (c) Chang, L. S.; Johnson, M. P.; Fink, M. J. Organometallics 1991, 10, 1219 and references cited therein.
14. Araki, S.; Imai, A.; Shimizu, K; Yamada, M.; Mori, A.; Butsugan, Y. J. Org. Chem. 1995, 60, 1841 (allylation of allylindiums).
15. (a) Takai, K.; Yamada, M.; Odaka, H.; Utimoto, K.; Fujii, T.; Furukawa, I. Chem. Lett. 1993, 315 (allyl-Ta).
16. (b) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685 (allyl-Zr).
17. (c) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834 (allyl-Zn).
18. (d) Molander, G. A. J. Org. Chem. 1983, 48, 5409 (allyl-Zn).
19. (e) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863 (allyl-Al).
20. (f) Negishi, E.; Miller, J. A. J. Am. Chem. Soc. 1983, 705, 6761 (allyl-Zn).
21. (g) Eishi, J. J.; Boleslawski, M. P. J. Organomet. Chem. 1987, 334, C1 (allyl-Ti).
22. (h) Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159 (allyl-Si).
23. Jung and co-workers reported cis-allylsilylation of phenylacetylene (ref 6h). However, their stereochemical assignment of 2-phenyl1,4-pentadiene is wrong: A proton that appeared at 5.12 ppm was assigned as Ha and that at 5.42 ppm as Hb. NOE experiments revealed that the Ha proton appears at 5.42 ppm and the Hb proton appears at 5.12 ppm. NOEs were observed at aromatic protons when a proton at 5.42 ppm was irradiated, and those were observed at Hc and Hd protons when a proton at 5.12 ppm was irradiated. (Matrix Presented)
24. Negishi reported that allylaluminums add to unactivated acetylenes in a cis-manner in the presence of Zr-catalyst (ref 6e). The present addition proceeds in trans-manner. Accordingly, it seems that the allylaluminum species is not involved as a reactive intermediate.
25. 4-catalyzed hydrostannylation, see: Asao, N.; Liu, J.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 2405.