Alkynyl germatranes as alternative reagents for the preparation of biarylethynes

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 451-453

  Faller, Jack W ^a   Kultyshev, Roman G ^a   Parr, Jonathan ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; CHLORIDE; FLUORIDE ION; PALLADIUM; PHOSPHINE; REAGENT; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYST; CHEMICAL REACTION;

EID: 0037433929     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02595-9     Document Type: Article

References (28)

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18. For Si reagents, see: (a) Hatanaka, Y.; Hiyama, T. Pure Appl. Chem. 1994, 66, 1471; (b) Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.; Hiyama, T. J. Org. Chem. 2000, 65, 5342; (c) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821; (d) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684. For Sn reagents, see: (e) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York; 1998.
19. For Si reagents, see: (a) Hatanaka, Y.; Hiyama, T. Pure Appl. Chem. 1994, 66, 1471; (b) Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.; Hiyama, T. J. Org. Chem. 2000, 65, 5342; (c) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821; (d) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684. For Sn reagents, see: (e) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York; 1998.
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21. Faller, J. W.; Kultyshev, R. G. Organometallics 2002, in press.
22. 2 (1.0 mL). Preparative TLC (silica gel, hexanes) allowed isolation of the biarylethyne product as the most mobile fraction.
23. 18.
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28. The coupling reaction between 1-aza-5-germa-5-phenylethynylbicyclo[3.3.3]undecane with an aryl bromide yields biarylethyne, see: Kosugi, M.; Tanji, T.; Tanaka, Y.; Yoshida, A.; Fugami, K.; Kameyama, M.; Magita, T. J. Organometal. Chem. 1996, 508, 255. The reaction required heating at 120°C for 24 h. The phenylethynyl germanium reagent was prepared from the chloride in 11% yield.