Cross-coupling reactions of aryl chlorides with organochlorosilanes: Highly effective methods for arylation or alkenylation of aryl chlorides

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7232-7233

  Gouda, Ken Ichi ^a   Hagiwara, Emiko ^a   Hatanaka, Yasuo ^a,c   Hiyama, Tamejiro ^b  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000121752     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9611172     Document Type: Article

References (37)

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20. The cross-coupling reactions of arylboronic acid with chlorobenzonitirile have been briefly reported: Poetsch, E.; Meyer, V. Abstracts of Papers, Seventh IUPAC Symposium on Organometallic Chemistry Directed towards Organic Synthesis, Kobe, Japan, 1993; S-20.
21. Aryl- and alkenylhalosilanes undergo the palladium-catalyzed cross-coupling reactions with organic halides and triflates in the presence of a fluoride salt, which activates the Si-C bonds of the silicon reagents by forming an anionic pentacoordinate silicate to promote the transmetalation with a palladium catalyst; see: (a) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 28, 8301. For reviews on the cross-coupling reactions of organosilicon compounds, see: (b) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845. Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471. Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (e) Horn, K. A. Chem. Rev. 1995, 95, 1317.
22. Aryl- and alkenylhalosilanes undergo the palladium-catalyzed cross-coupling reactions with organic halides and triflates in the presence of a fluoride salt, which activates the Si-C bonds of the silicon reagents by forming an anionic pentacoordinate silicate to promote the transmetalation with a palladium catalyst; see: (a) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 28, 8301. For reviews on the cross-coupling reactions of organosilicon compounds, see: (b) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845. Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471. Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (e) Horn, K. A. Chem. Rev. 1995, 95, 1317.
23. Aryl- and alkenylhalosilanes undergo the palladium-catalyzed cross-coupling reactions with organic halides and triflates in the presence of a fluoride salt, which activates the Si-C bonds of the silicon reagents by forming an anionic pentacoordinate silicate to promote the transmetalation with a palladium catalyst; see: (a) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 28, 8301. For reviews on the cross-coupling reactions of organosilicon compounds, see: (b) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845. Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471. Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (e) Horn, K. A. Chem. Rev. 1995, 95, 1317.
24. Aryl- and alkenylhalosilanes undergo the palladium-catalyzed cross-coupling reactions with organic halides and triflates in the presence of a fluoride salt, which activates the Si-C bonds of the silicon reagents by forming an anionic pentacoordinate silicate to promote the transmetalation with a palladium catalyst; see: (a) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 28, 8301. For reviews on the cross-coupling reactions of organosilicon compounds, see: (b) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845. Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471. Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (e) Horn, K. A. Chem. Rev. 1995, 95, 1317.
25. Aryl- and alkenylhalosilanes undergo the palladium-catalyzed cross-coupling reactions with organic halides and triflates in the presence of a fluoride salt, which activates the Si-C bonds of the silicon reagents by forming an anionic pentacoordinate silicate to promote the transmetalation with a palladium catalyst; see: (a) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 28, 8301. For reviews on the cross-coupling reactions of organosilicon compounds, see: (b) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845. Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471. Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (e) Horn, K. A. Chem. Rev. 1995, 95, 1317.
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35. 1H NMR and GLC (OV-101, TCD).
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