New alkynyl amides by negishi coupling

Synlett

Volumn , Issue 5, 2004, Pages 783-786

  Rodríguez, David ^a   Castedo, Luis ^a   Saá, Carlos ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Alkynes; Negishi reaction; Ynamides

Indexed keywords

ALKYNYL GROUP; AMIDE; IODIDE; PALLADIUM; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; EXPERIMENT; STRUCTURE ANALYSIS;

EID: 1942489645     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817785     Document Type: Article

References (19)

1. (a) For a recent review of ynamides and ynamines, see: Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
2. (b) See also: Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379.
3. (c) Viehe, H. G. Chemistry of Acetylenes; Marcel Dekker: New York, 1969, Chap. 12, 861-912.
4. (d) Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1967, 6, 767.
5. (e) Himbert, G. In Methoden der Organischen Chemie (Houben-Weyl); Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3267-3443.
6. (a) Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. 1998, 37, 489.
7. (b) Brückner, D. Synlett 2000, 1402.
8. (c) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
9. (d) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
10. (e) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011.
11. (a) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708.
12. (b) For a related reaction, see: Löffler, A.; Himbert, G. Synthesis 1994, 383.
13. Selected publications: (a) Rodríguez, D.; Navarro, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (b) Rodríguez, D.; Navarro, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (c) Rodríguez, D.; Castedo, L.; Domínguez, D.; Saá, C. Org. Lett. 2003, 5, 3119.
14. Selected publications: (a) Rodríguez, D.; Navarro, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (b) Rodríguez, D.; Navarro, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (c) Rodríguez, D.; Castedo, L.; Domínguez, D.; Saá, C. Org. Lett. 2003, 5, 3119.
15. Selected publications: (a) Rodríguez, D.; Navarro, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (b) Rodríguez, D.; Navarro, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (c) Rodríguez, D.; Castedo, L.; Domínguez, D.; Saá, C. Org. Lett. 2003, 5, 3119.
16. For a comprehensive review of the palladium-catalyzed cross-coupling, see: Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis, Part 3, Vol. 1; Wiley-Interscience: New York, 2002, 215-1119.
17. As far as we know, there has been a report of Sonogashira coupling of an ynamine but not of any amide. Whether or not an ynamine dimer analogous to 8 was also produced in Liao et al's reaction is not known, because they used a solid support for their aryl iodide and washed away all components of the reaction mixture other than the cross-coupled product. See: Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815.
18. For homocoupling of 1-alkynyl tosylamides, see: Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377.
19. +], 150 (37), 91 (100)