Nickel-promoted alkylative or arytative carboxylation of alkynes

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3345-3347

  Takimoto, Masanori ^a   Shimizu, Kazuya ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

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ARTICLE;

EID: 0000740782     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016585z     Document Type: Article

References (26)

1. Reviews: (a) Behr, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 661.
2. (b) Braunstein, P. B.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747.
3. (c) Gibson, D. H. Chem. Rev. 1996, 96, 2063.
4. (d) Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2207.
5. (a) Hoberg, H.; Burkhart, G. Angew. Chem., Int. Ed. Engl. 1982, 21, 76.
6. (b) Hoberg, H.; Schäfer, D. J. Organomet. Chem. 1982, 238, 383.
7. (c) Hoberg, H.; Schäfer, D.; Burkhar, G.; Krüger, C.; Romao, M. J. J. Organomet. Chem. 1984, 266, 203.
8. (d) Saito, S.; Nakagawa, S.; Koizumi, T.; Hirayama, K.; Yamamoto, Y. J. Org. Chem. 1998, 64, 3975.
9. Recent reports of catalytic reactions involving a related coupling process: (a) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329.
10. (b) Tsuda, T.; Morikawa, S.; Hasegawa, N.; Saesusa, T. J. Org. Chem. 1990, 55, 2978.
11. (d) Dèrien, S.; Clinet, J.-C.; Duñach, E.; Pèrichon, J. J. Am. Chem. Soc. 1991, 113, 8447.
12. Dunach also reported a nickel-catalyzed electrochemical carboxylation of terminal alkynes which afforded α-substituted-α,β-unsaturated acid in a reverse regioselectivity. (a) Duñach, E.; Pèrichon, J. J. Organomet. Chem. 1988, 352, 239.
13. (b) Duñach, E.; Pèrichon, J. J. Organomet. Chem. 1990, 385, C43. See also ref 3d.
14. Transmetalation processes of structurally related oxanickelacycles with organozinc reagents were already reported by Montgomery. (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
15. (b) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
16. 2 with organozinc reagents which was based on a similar concept. Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2001, 123, 2895.
17. 2 was unsuccessful and 3a was obtained in only 30% yield.
18. For the preparation of benzylzinc bromide, see: Berk, S. C.; Knochel, P.; Yeh, M. C. P. J. Org. Chem. 1988, 53, 5789.
19. Butylzinc iodide was prepared from butyl iodide and metallic zinc according to a method described in the following report. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
20. Reviews for functionalized zinc reagents: (a) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
21. (b) Rieke, R. D. Aldrichimica Acta 2000, 33, 52. For the preparation of specific zinc reagents that appear in Table 3, see refs 11-13.
22. Arylzinc iodide 13: Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.
23. Reformatsky reagent 14: (a) Curé, J.; Gaudemar, M. Bull. Soc. Chim. Fr. 1968, 8, 3224.
24. (b) Curé, J.; Gaudemar, M. Bull. Soc. Chim. Fr. 1969, 9, 2471.
25. For the preparation of organozinc reagents 15 and 16, see ref 9.
26. 2, since the nucleophilicity of 14 is higher than that of other organozinc reagents.