NaOH-Promoted cross-coupling reactions of organosilicon compounds with organic halides: Practical routes to biaryls, alkenylarenes and conjugated dienes

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 439-442

  Hagiwara, Emiko ^a   Gouda, Ken Ichi ^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

BENZENE DERIVATIVE; BIPHENYL DERIVATIVE; ORGANIC COMPOUND; ORGANOSILICON DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; TECHNIQUE;

EID: 0031023975     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02320-9     Document Type: Article

References (21)

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2. (b) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471-1478.
3. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448.
4. (d) Horn, K. A. Chem. Rev. 1995, 95, 1317-1350.
5. Recently, we have found that the palladium-catalyzed coupling reaction of allylic carbonates with alkenylfluorosilanes proceeds in the absence of fluoride salts. Matsuhashi, H.; Hatanaka, Y.; Hiyama, Kuroboshi, M. Tetrahedron Lett. 1995, 36, 1539-1540.
6. 3 (4.1 mg, 0.015 mmol) in benzene (1 ml) at room temperature for 40 min, were added. The reaction mixture was heated at 80 °C for 39 h with vigorous stirring. The usual work up of the reaction mixture, followed by column chromatography (silica-gel, ethyl acetate : hexane = 1: 7) gave a 275 mg of 4-acetyl-1,1′-biphenyl as a colorless solid (1.4 mmol, 89%). The physical properties of the obtained product were in good agreement with the reported data: Long, L. M.; Henze, H. R. J.Am. Chem. Soc. 1941, 63, 1939-1940.
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