Palladium-catalyzed syntheses of oxygen- and nitrogen heterocycles via transmetalation of functionalized alkynyl stannanes

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 643-646

  Chandrasekharam, M ^a   Chang, Shie Tsung ^a   Liang, Kwei Wen ^a   Li, Wen Tai ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST;

EID: 0032510021     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10707-9     Document Type: Article

References (15)

1. (1) a) Lozar, L. D.; Clark, R. D.; Heathcock, C. H. J. Org. Chem., 1977, 42, 1386.
2. b) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett., 1978, 26, 3201.
3. c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R.; Boots, D. R. J. Org. Chem. 1980, 45, 1254.
4. (2) a) Herndon, J. W. ; Wu, C. Synlett 1990, 1, 411.
5. b) Danheiser, R. L. ; Takahashi, T.; Bertok, R.; Dixon, B. R. Tetrahydon Lett., 1993, 34, 3845.
6. c) Danheiser, R. L. ; Ksasigroch, C. A. ; Tsai Y. M. J. Am. Chem. Soc. 1985, 107, 7233.
7. d) Panek, J. S. ; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868.
8. (3) a) Bruce, M. I. Chem. Rev. 1991, 91, 257.
9. b) Davidson, A.; Solar, J. P. J. Organometal. Chem. 1979, 166, C13.
10. (4) a) Liang, K.-W.; Li, W.-T.; Peng, S.-M.; Wang, S.-L.; Liu, R.-S., J. Am. Chem. Soc. 1997, 119, 4404.
11. b) Chen, C.-C.; Fan, J.-S.; Shieh, S.-J.; Lee, G.-H.; Peng, S.-M.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 1996, 118, 9279.
12. 3): 212.6, 110.4, 85.0, 74.3, 61.9, 26.4.
13. (6) For oxidative addition of Pd(0) species with metal-iodide M-I to form bimetallic M-Pd(II)-I species, see representative examples: a) Hoskins, B. F.; Steen, R. J.; Turney, T. W. J. Chem. Soc. Dalton. Trans. 1984, 1831.
14. b) Braunstein, P.; Knorr, P.; Tiripicchio, A.; Tiripicchio Carmellini, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1361.
15. 2I and unfunctionalized alkynyl stannanes, see the precedent example: Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301.