Palladium Pincer Complex-Catalyzed Trimethyltin Substitution of Functionalized Propargylic Substrates. An Efficient Route to Propargyl- and Allenyl-Stannanes

Journal of the American Chemical Society

Volumn 126, Issue 2, 2004, Pages 474-475

  Kjellgren, Johan ^a   Sundén, Henrik ^a   Szabó, Kálmán J ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENYLSTANNANE; FUNCTIONAL GROUP; PALLADIUM; PROPARGYLSTANNANE; TIN DERIVATIVE; TRIMETHYLTIN; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTRON; OXIDATION; SYNTHESIS;

EID: 0345825802     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0391715     Document Type: Article

References (20)

1. Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435.
2. (a) Mitchell, T. N.; Killing, A. A. H.; Rutschow, D. J. Organomet. Chem. 1986, 304, 257.
3. (b) Piers, E.; Skrelj, R. T. Chem. Soc., Chem. Commun. 1986, 626.
4. (c) Mabon, R.; Richecoeur, A. M. E.; Sweeney, J. B. J. Org. Chem. 1999, 64, 328.
5. (d) Tsuji, Y.; Nishiyama, K.; Hori, S.-i.; Ebihara, M.; Kawamura, T. Organometallics 1998, 17, 507.
6. (e) Hua, R.; Onozawa, S.-y.; Tanaka, M. Organometallics 2000, 19, 3269.
7. (f) Manusco, J.; Lautens, M. Org. Lett. 2003, 1653.
8. Solin, N.; Kjellgren, J.; Szabó, K. J. Angew. Chem., Int. Ed. 2003, 42, 3656.
9. (a) Albrect, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3751.
10. (b) Singleton, J. T. Tetrahedron 2003, 59, 1837.
11. (a) Alsters, P. L.; Baesjou, P. J.; Janssen, M. D.; Kooijman, H.; Sicherer-Roetman, A.; Spek, A. L.; van Koten, G. Organometallics 1992, 11, 4124.
12. (b) Rimml, H.; Venanzi, L. M. J. Organomet. Chem. 1983, 259, C6.
13. 8 at 25 °C.
14. 3): 129.0 ppm. Wrackmeyer, B. Annual Reports on NMR Spectroscopy; Academic Press: London, 1985: Vol 16. p 73.
15. Formation of the allenic product 6 in the presence of electron-withdrawing substituents can be ascribed to the polarization of the π-system of the triple bond. As a consequence, the carbon atom attached to the electron-withdrawing substituent is activated toward nucleophilic attack by the trimethyltin ligand of 1c.
16. (a) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589.
17. (b) Elsevier, C. J.; Kleijn, H.; Boersma, J.; Vermeer, P. Organometallics 1986, 5, 716.
18. (a) Marshall, J. A. Chem. Rev. 1996, 96, 31.
19. (b) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1992, 57, 1242.
20. (c) Ruitenberg, K.; Westmijze, H.; Meijer, C. J.; Elsevier, C. J.; Vermeer, P. J. J. Organomet. Chem. 1983, 241, 417.