Hiyama cross-coupling of chloro-, fluoro-, and methoxypyridyltrimethylsilanes: Room-temperature novel access to functional bi(het)aryl

Organic Letters

Volumn 7, Issue 4, 2005, Pages 697-700

  Pierrat, Philippe ^a   Gros, Philippe ^a   Fort, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE DERIVATIVE; FLUORINE DERIVATIVE; HALIDE; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; CROSS COUPLING REACTION; REACTION TIME; ROOM TEMPERATURE;

EID: 14844349847     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047482u     Document Type: Article

References (28)

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2. For reviews, see: (a) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Weinheim, Germany, 1998. (b) Hiyama, T. J. Organomet. Chem. 2002, 653, 58-61. (c) Denmark, S. E.; Sweiss, R. F. Acc. Chem. Res., 2002, 35, 835-846. (d) Spivey, A. C.; Gripton, C. J. G.; Hannah, J. P. Curr. Org. Synth. 2004, 1, 211-226.
3. For reviews, see: (a) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Weinheim, Germany, 1998. (b) Hiyama, T. J. Organomet. Chem. 2002, 653, 58-61. (c) Denmark, S. E.; Sweiss, R. F. Acc. Chem. Res., 2002, 35, 835-846. (d) Spivey, A. C.; Gripton, C. J. G.; Hannah, J. P. Curr. Org. Synth. 2004, 1, 211-226.
4. For reviews, see: (a) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Weinheim, Germany, 1998. (b) Hiyama, T. J. Organomet. Chem. 2002, 653, 58-61. (c) Denmark, S. E.; Sweiss, R. F. Acc. Chem. Res., 2002, 35, 835-846. (d) Spivey, A. C.; Gripton, C. J. G.; Hannah, J. P. Curr. Org. Synth. 2004, 1, 211-226.
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19. For preparation of 1-3 with BuLi-LiDMAE, see: Choppin, S. Gros, Ph. Fort, Y. Org. Lett. 2000, 2, 803-805. Choppin, S. Gros, Ph. Fort, Eur. J. Org. Chem. 2001, 3, 603-606. For preparation of 5 and 6 with LDA or LTMP, see: Gribble, G. W. Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137-4140. Comins, D. L.; Myoung, Y. J. Org. Chem. 1990, 55, 292-298. Compound 4 was prepared by reaction of BuLi with 2-chloro-5-bromopyridine in THF at -78°C and quenching with TMSC1.
20. For preparation of 1-3 with BuLi-LiDMAE, see: Choppin, S. Gros, Ph. Fort, Y. Org. Lett. 2000, 2, 803-805. Choppin, S. Gros, Ph. Fort, Eur. J. Org. Chem. 2001, 3, 603-606. For preparation of 5 and 6 with LDA or LTMP, see: Gribble, G. W. Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137-4140. Comins, D. L.; Myoung, Y. J. Org. Chem. 1990, 55, 292-298. Compound 4 was prepared by reaction of BuLi with 2-chloro-5-bromopyridine in THF at -78°C and quenching with TMSC1.
21. For preparation of 1-3 with BuLi-LiDMAE, see: Choppin, S. Gros, Ph. Fort, Y. Org. Lett. 2000, 2, 803-805. Choppin, S. Gros, Ph. Fort, Eur. J. Org. Chem. 2001, 3, 603-606. For preparation of 5 and 6 with LDA or LTMP, see: Gribble, G. W. Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137-4140. Comins, D. L.; Myoung, Y. J. Org. Chem. 1990, 55, 292-298. Compound 4 was prepared by reaction of BuLi with 2-chloro-5-bromopyridine in THF at -78°C and quenching with TMSC1.
22. For preparation of 1-3 with BuLi-LiDMAE, see: Choppin, S. Gros, Ph. Fort, Y. Org. Lett. 2000, 2, 803-805. Choppin, S. Gros, Ph. Fort, Eur. J. Org. Chem. 2001, 3, 603-606. For preparation of 5 and 6 with LDA or LTMP, see: Gribble, G. W. Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137-4140. Comins, D. L.; Myoung, Y. J. Org. Chem. 1990, 55, 292-298. Compound 4 was prepared by reaction of BuLi with 2-chloro-5-bromopyridine in THF at -78°C and quenching with TMSC1.
23. Other fluoride sources (TMAF, CsF, polymer-supported fluoride) gave low yields.
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25. Mulliken charges calculated using semiempirical PM3 method.
26. 4) of the organic layer, the solvents were evaporated under reduced pressure and the crude product purified by column chromatography.
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28. Normant, J. F. Synthesis 1972, 63.