Cobalt-catalyzed mono-coupling of R3SiCH2MgCl with 1,2-dihalogenoethylene: A general route to γ-substituted (E)-allylsilanes

Tetrahedron Letters

Volumn 45, Issue 24, 2004, Pages 4677-4679

  Kamachi, Taku ^a   Kuno, Akiko ^a   Matsuno, Chikashi ^a   Okamoto, Sentaro ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

Allylsilane; Co catalyst; Cross coupling

Indexed keywords

ACETONE; COBALT; ETHYLENE DERIVATIVE; MAGNESIUM CHLORIDE; NICKEL; ORGANOMETALLIC COMPOUND; PALLADIUM; PROPYLENE; SILANE DERIVATIVE; TRIMETHYLSILYLMETHYLMAGNESIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; GRIGNARD REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SUZUKI REACTION;

EID: 2442719958     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.098     Document Type: Article

References (15)

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3. For synthesis of γ-substituted allylsilanes, see: Thibaudeau S., Gouverneur V. Org. Lett. 5:2003;4891. and references cited therein
4. 3SiH and the following methylation with MeMgBr. For preparation and synthetic utilization of 2, see: for 2a, Ochiai M., Fujita E. J. Chem. Soc., Chem. Commun. 1980;1118
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9. 2Cl and magnesium turnings in ether or THF and titrated by using acid and base. Yields shown in Table 1 and Scheme 2 were based on the amount of the Grignard reagent used
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12. 3, 500 MHz): 2a: δ 5.87 (dt, J=13, 8.5 Hz, 1H), 5.51 (d, J=13 Hz, 1H), 1.48 (d, J=8.5 Hz, 2H), 0.03 (s, 9H); 2b: δ 6.16 (dt, J=13, 8.5 Hz, 1H), 5.82 (dt, J=13, 1.0 Hz, 1H), 1.52 (dd, J=1.0, 8.5 Hz, 2H), 0.06 (s, 9H); 4: δ 7.39-7.57 (m, 5H), 5.90 (ddt, J=1.0, 13, 8.5 Hz, 1H), 5.77 (dd, J=1.0, 13 Hz, 1H), 1.75 (d, J=8.5 Hz, 2H), 0.35 (s, 6H)
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15. 2-mediated reaction of 2b with aldehydes providing δ-trimethylsilyl allylic alcohols has been reported: see Refs. [3d, e]