32193-90-1Relevant academic research and scientific papers
Method for synthesizing (E)-Anethol and Related Compounds By Cross Coupling Reaction of Potassium alllyltrifluroborate and 4-bromoanisole and aryl halides
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Page/Page column 4, (2012/01/15)
Methods of producing substituted and non-substituted beta-methyl styrene by a cross-coupling reaction are provided. The disclosure also provides for methods of preparing (E)-Anethol and related compounds by a cross coupling reaction of potassium allyltrifluoroborate and 4-bromoanisole and aryl halides. Compounds, compositions, and methods of treating disorders utilizing beta-methyl styrene are also provided.
Gas-phase pyrolytic reaction of 4-Aryl-3-buten-2-ols and allyl benzyl ethers: Kinetic and mechanistic study
Al-Etaibi, Alya M.,Al-Awadi, Nouria A.,Ibrahim, Maher R.,Ibrahim, Yehia A.
experimental part, p. 407 - 419 (2010/05/02)
Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CHCH(CHs)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO2] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH2, where Ar is Ph, p-MeO, p-Me, p-Cl, pNO2) and 7-×-1,2-dihydronaphthalene derivatives (where X is H, MeO); FVP of 1-aryl-3benzyloxyl-1-butenes and benzyl cinnamyl ethers [ArCH=CHCH(X)OCH2Ph, where Ar is phenyl, p-MeO, p-Me, p-Cl, X is H, Me, Ph] gave the corresponding but-2-en-l-ylbenzene derivatives (ArCH 2CH=CH-X, where X is H, Me, Ph) together with benzaldehyde. The proposed mechanism of these pyrolytic transformations was supported by kinetic and product analysis.
Remarkable regioselectivity in microwave-enhanced palladium-catalyzed allylation reaction involving allyltrifluoroborates and aryl halides
Al-Masum, Mohammad,Alam, Shahrina
scheme or table, p. 5201 - 5204 (2009/12/06)
An unprecedented cross-coupling reaction of potassium allyltrifluoroborates and aryl halides to the corresponding trans-β-methylstyrenes in the presence of PdCl2(dtbpf) catalyst under microwave heating was developed.
Cross-coupling of aromatic bromides with allylic silanolate salts
Denmark, Scott E.,Werner, Nathan S.
supporting information; experimental part, p. 16382 - 16393 (2009/05/08)
The sodium salts of allyldimethylsilanol and 2-butenyldimethylsilanol undergo palladium-catalyzed cross-coupling with a wide variety of aryl bromides to afford allylated and crotylated arenes. The coupling of both silanolates required extensive optimization to deliver the expected products in high yields. The reaction of the allyldimethylsilanolate takes place at 85°C in 1,2-dimethoxyethane with allylpalladium chloride dimer (2.5 mol %) to afford 73-95% yields of the allylation products. Both electron-rich and sterically hindered bromides reacted smoothly, whereas electron-poor bromides cross-coupled in poor yield because of a secondary isomerization to the 1-propenyl isomer (and subsequent polymerization). The 2-butenyldimethylsilanolate (E/Z, 80:20) required additional optimization to maximize the formation of the branched (γ-substitution) product. A remarkable influence of added alkenes (dibenzylideneacetone and norbornadiene) led to good selectivities for electron-rich and electron-poor bromides in 40-83% yields. However, bromides containing coordinating groups (particularly in the ortho position) gave lower, and in one case even reversed, selectivity. Configurationally homogeneous (E)-silanolates gave slightly higher γ-selectivity than the pure (Z)-silanolates. A unified mechanistic picture involving initial γ-transmetalation followed by direct reductive elimination or σ-π isomerization can rationalize all of the observed trends.
