Room temperature palladium catalysed coupling of acyl chlorides with terminal alkynes

Chemical Communications

Volumn , Issue 8, 2005, Pages 1037-1039

  Cox, Russell J ^a   Ritson, Dougal J ^a   Dane, Thomas A ^a   Berge, John ^b   Charmant, Jonathan P H ^a   Kantacha, Anob ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CHLORIDE; COPPER DERIVATIVE; KETONE; PALLADIUM;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; OXIDATION; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 14944357257     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b414826f     Document Type: Article

References (17)

1. M. E. Krafft, L. V. R. Bonaga, A. S. Felts, C. Hirosawa and S. Kerrigan, J. Org. Chem., 2003, 68, 6039-6042; J.-C. Wang, S.-S. Ng and M. J. Krische, J. Am. Chem. Soc., 2003, 125, 3682-3683.
2. M. E. Krafft, L. V. R. Bonaga, A. S. Felts, C. Hirosawa and S. Kerrigan, J. Org. Chem., 2003, 68, 6039-6042; J.-C. Wang, S.-S. Ng and M. J. Krische, J. Am. Chem. Soc., 2003, 125, 3682-3683.
3. P. Wipf, Y. Aoyama and T. E. Benedum, Org. Lett., 2004, 6, 3593-3595.
4. M. Kunishima, D. Nakata, S. Tanaka, K. Hioki and S. Tani, Tetrahedron, 2000, 56, 9927-9935; M. J. Piggott and D. Wege, Aust. J. Chem., 2000, 53, 749-754.
5. M. Kunishima, D. Nakata, S. Tanaka, K. Hioki and S. Tani, Tetrahedron, 2000, 56, 9927-9935; M. J. Piggott and D. Wege, Aust. J. Chem., 2000, 53, 749-754.
6. D. Rodriguez, M. F. Martinez-Esperon, L. Castedo, D. Dominguez and C. Saa, Synlett, 2003, 10, 1524-1526.
7. P. Fitton, M. P. Johnson and J. E. McKeon, J. Chem. Soc., Chem. Commun., 1968, 6.
8. G. W. Kabalka, R. R. Malladi, D. Tejedor and S. Kelly, Tetrahedron Lett., 2000, 41, 999-1001; H. Chen and M.-Z. Deng, Org. Lett., 2000, 2, 1649-1651.
9. G. W. Kabalka, R. R. Malladi, D. Tejedor and S. Kelly, Tetrahedron Lett., 2000, 41, 999-1001; H. Chen and M.-Z. Deng, Org. Lett., 2000, 2, 1649-1651.
10. M. R. Eberhard, Org. Lett., 2004, 6, 2125-2128.
11. Y. Tohda, K. Sonogashira and N. Hagihara, Synthesis, 1977, 11, 777-778.
12. D. A. Alonso, C. Najera and M. C. Pacheco, J. Org. Chem., 2004, 69, 1615-1619.
13. L. Hintermann and A. Togni, Heb. Chim. Acta, 2000, 83, 2425-2435; R. W. Holder, H. S. Freiman and M. F. Stefanchick, J. Org. Chem., 1976, 41, 20, 3303-3307; C. D. Hurd and C. A. Blanchard, J. Am. Chem. Soc., 1950, 72, 1461-1462.
14. L. Hintermann and A. Togni, Heb. Chim. Acta, 2000, 83, 2425-2435; R. W. Holder, H. S. Freiman and M. F. Stefanchick, J. Org. Chem., 1976, 41, 20, 3303-3307; C. D. Hurd and C. A. Blanchard, J. Am. Chem. Soc., 1950, 72, 1461-1462.
15. L. Hintermann and A. Togni, Heb. Chim. Acta, 2000, 83, 2425-2435; R. W. Holder, H. S. Freiman and M. F. Stefanchick, J. Org. Chem., 1976, 41, 20, 3303-3307; C. D. Hurd and C. A. Blanchard, J. Am. Chem. Soc., 1950, 72, 1461-1462.
16. E. D. Dobrzynski and R. E. Angelici, Inorg. Chem, 1975, 14, 59-63.
17. 2 in these reactions appeared to increase the rate of formation, and the yield, of amide and carbamate products.