Copper-catalyzed cross-coupling of alkyl and aryl grignard reagents with alkynyl halides

Angewandte Chemie - International Edition

Volumn 49, Issue 7, 2010, Pages 1278-1281

  Cahiez, Gérard ^a   Gager, Olivier ^a   Buendia, Julien ^a  

^a CNRS   (France)

Author keywords

Alkynes; Copper; Cross coupling; Grignard reagents

Indexed keywords

ALKYNYLS; CHEMICAL EQUATIONS; CHEMOSELECTIVE; COPPER CATALYSIS; CROSS-COUPLING; CROSS-COUPLINGS; FUNCTIONALIZED; GRIGNARD REAGENT; HIGH YIELD; INTERNAL ALKYNES; N-METHYL PYRROLIDINONE;

ACETYLENE; CHEMICAL REACTIONS;

COPPER;

EID: 76349085438     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905816     Document Type: Article

References (37)

1. a) Preparative Acetylenic Chemistry, 2nd ed. (Ed. : L. Brandsma), Elsevier, Amsterdam, 1988, chap. 3, p. 39-40;
2. b) M. Buck, J. M. Chong, Tetrahedron Lett. 2001, 42, 5825;
3. Recently, a few reports on alkyl-alkynyl coupling through a palladium- or a nickelcatalyzed Sonogashira reaction were published, see: c) E. Eckhardt, G. Fu, J. Am. Chem. Soc. 2003, 125, 13642;
4. d) G. Altenhoff, S. Würtz, F. Glorius, Tetrahedron Lett. 2006, 47, 2925;
5. e) O. Vechorkin, D. Barmaz, V. Proust, X. Hu, J. Am. Chem. Soc. 2009, 131, 12078.
6. E.-i. Negishi, S. Baba, J. Am. Chem. Soc. 1975, 97, 7385.
7. M. S. Kharasch, F. L. Lambert, M. H. Ury, J. Org. Chem. 1945, 10, 298.
8. H. K. Black, D. H. S. Horn, B. C. L. Weedon, J. Chem. Soc. 1954, 1704.
9. G. Giacomelli, L. Lardicci, Tetrahedron Lett. 1978, 19, 2831.
10. M. C. P. Yeh, P. Knochel, Tetrahedron Lett. 1989, 30, 4799.
11. R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874.
12. R. Oliver, D. R. M. Walton, Tetrahedron Lett. 1972, 13, 5209.
13. A. Commerçon, J. F. Normant, J. Villiéras, Tetrahedron 1980, 36, 1215.
14. a) G. Cahiez, C. Chaboche, M. Jézéquel, Tetrahedron 2000, 56, 2733 ;
15. For a similar Cu-catalyzed reaction with organomanganese reagents, see: b) G. Cahiez, S. Marquais, Synlett 1993, 45;
16. c) G. Cahiez, S. Marquais, Pure Appl. Chem. 1996, 68, 53.
17. J. Terao, H. Todo, S. A. Begum, H. Kuniyasu, N. Kambe, Angew. Chem. 2007, 119, 2132;
18. Angew. Chem. Int. Ed. 2007, 46, 2086.
19. In the case of the copper-catalyzed alkylation or Grignard reagents, we have previously observed that the presence of NMP is not always beneficial. See referefences [10b,c].
20. L. Boymond, M. Rottländer, G. Cahiez, P. Knochel, Angew. Chem. 1998, 110, 1801;
21. Angew. Chem. Int. Ed. 1998, 37, 1701.
22. G Cahiez, C. Duplais, J. Buendia, Angew. Chem. 2009, 121, 6859;
23. Angew. Chem. Int. Ed. 2009, 48, 6731.
24. a) H. Gilman, A. G. Brook, L. S. Miller, J. Am. Chem. Soc. 1953, 75, 4531;
25. b) C. Eaborn, A. R. Thompson, D. R. M. Walton, J. Chem. Soc. 1967, 1364;
26. c) B. W. Metcalf, K. Jund, Tetrahedron Lett. 1977, 18, 3689.
27. The chlorination of 2-cyanophenylacetylene was performed according to: R. Truchet, Ann. Chim. 1931, 16, 309. The procedure has been slightly modified as described in the Supporting Information.
28. M. B. Nielsen, F. Diederich, Chem. Rev. 2005, 105, 1837.
29. J. F. Normant, A. Alexakis, G. Cahiez, J. Villiéras, C. R. Acad. Sci. Ser. C 1974, 279, 763.
30. a) J. F. Normant, G. Cahiez, C. Chuit, A. Alexakis, J. Villiéras, J. Organomet. Chem. 1972, 40, C49;
31. b) J. F. Normant, G. Cahiez, C. Chuit, J. Villiéras, Tetrahedron Lett. 1973, 14, 2407;
32. c) J. F. Normant, G. Cahiez, C. Chuit, J. Villiéras, J. Organomet. Chem. 1973, 54, C53;
33. d) J. F. Normant, G. Cahiez, M. Bourgain, C. Chuit, J. Villiéras, Bull. Soc. Chim. Fr. 1974, 1656;
34. e) J. F. Normant, G. Cahiez, C. Chuit, J. Villiéras, J. Organomet. Chem. 1974, 77, 269;
35. f) J. F. Normant, G. Cahiez, C. Chuit, J. Villiéras, J. Organomet. Chem. 1914, 77, 281.
36. For a review see: g) A. Alexakis, J. F. Normant, Synthesis 1981, 841.
37. H. Westmijze, H. Kleijn, P. Vermeer, Reel. Trav. Chim. Pays-Bas 1980, 98.