Allylation of Unactivated and/or Functionalized Alkynes with Allylindiums

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2318-2319

  Fujiwara, Naoya ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000125198     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9701041     Document Type: Article

References (29)

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 organoLi, -Mg, and -Zn and catalytic Ni, Pd, and 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 organoLi, -Mg, and -Zn and catalytic Ni, Pd, and 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 organoLi, -Mg, and -Zn and catalytic Ni, Pd, and 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 organoLi, -Mg, and -Zn and catalytic Ni, Pd, and 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 organoLi, -Mg, and -Zn and catalytic Ni, Pd, and 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 organoLi, -Mg, and -Zn and catalytic Ni, Pd, and 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. (a) Takai, K.; Yamada, M.; Odaka, H.; Utimoto, K.; Fujii, T.; Furukawa, I. Chem. Lett. 1995, 315 (allyl-Ta).
9. (b) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685 (allyl-Zr).
10. (c) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834 (allyl-Zn).
11. (d) Molander, G. A. J. Org. Chem. 1983, 48, 5409 (allyl-Zn).
12. (e) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863 (allyl-Al).
13. (f) Negishi, E.; Miller, J. A. J. Am. Chem. Soc. 1983, 105, 6761 (allyl-Zn).
14. (g) Eishi, J. J.; Boleslawski, M. P. J. Organomet. Chem. 1987, 334, C1 (allyl-Ti).
15. (h) Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159 (Lewis acid-catalyzed allyl-Si).
16. (i) Asao, N.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1513 (Lewis acid-catalyzed allyl-Sn).
17. (j) Asao, N.; Yoshikawa, E.; Yamamoto, Y. J. Org. Chem. 1996, 4874 (Lewis acid-catalyzed allyl-Si).
18. Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831.
19. (a) Araki, S.; Imai, A.; Shimizu, K.; Yamada, M.; Mori, A.; Butsugan, Y. J. Org. Chem. 1995, 60, 1841.
20. (b) Araki, S.; Usui, H.; Kato, M.; Butsugan, Y. J. Am. Chem. Soc. 1996, 118, 4699.
21. 2O and aqueous/dry THF have been studied: (a) Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863. (b) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931. (c) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
22. 2O and aqueous/dry THF have been studied: (a) Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863. (b) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931. (c) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
23. 2O and aqueous/dry THF have been studied: (a) Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863. (b) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931. (c) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
24. 3 are used for the allylation reaction, and the third allyl group acts as a ligand of the In complex (ref4). Accordingly, 0.6 equiv of allylindium corresponds to 1.2 equiv of allylating agent in the ordinary sense.
25. Yamamoto, Y.; Yoshikawa, E. Unpublished results.
26. The allylation of TMS-substituted alkynes with allylzinc bromide gives the same regioselectivity as the present allylindation: Molander, G. A. J. Org. Chem. 1983, 48, 5409.
27. The allylindium reagent was prepared originally in DMF (ref 4). Since then, the allylindation reactions of acetylenes have been carried out in this solvent. Now, it is clear that the reagent can be prepared in THF, and this finding expands the scope of this reagent to the carboindation.
28. A double-zincation intermediate was proposed in the allylzincation of terminal alkynes: Frangin, Y.; Gaudemar, M. J. Organomet. Chem. 1977, 142, 9. See also: Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 883.
29. A double-zincation intermediate was proposed in the allylzincation of terminal alkynes: Frangin, Y.; Gaudemar, M. J. Organomet. Chem. 1977, 142, 9. See also: Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 883.