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Upstream product

• 774-48-1 (diethoxymethyl)benzene 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 19319-11-0 (Z)-1-phenyl-2-(trimethylsilyl)ethylene 
• 100-42-5 styrene 
• 944077-22-9 C₂₁H₁₇ClS 
• 33603-87-1 β-chlorocinnamaldehyde 
• 62668-02-4 (E)-1,3-diphenyl-2-propen-1-ol 

Relevant academic research and scientific papers

Metal-free and recyclable route to synthesize polysubstituted olefins via C-C bond construction from direct dehydrative coupling of alcohols or alkenes with alcohols catalyzed by sulfonic acid-functionalized ionic liquids

A direct synthesis of polysubstituted olefins via construction of C-C bonds, which involves the direct dehydrative coupling of alcohols or alkenes with alcohols, was realized using a series of alkanesulfonic acid group-functionalized ionic liquids (SO3H-functionlization ILs) without additives. The metal-free and recyclable catalyst system avoided the disposal and neutralization of acidic catalysts after reaction and tolerated a broad range of substrates, including benzylic, allyl, propargylic, aliphatic and aromatic or aliphatic olefins. Additionally, the catalytic system was suitable for a gram-scale preparation. Preliminary mechanistic studies indicated that the C-H bond cleavage in this reaction might be involved in the rate-determining step.

Sp3-sp2 C-C bond formation via Bronsted acid trifluoromethanesulfonic acid-catalyzed direct coupling reaction of alcohols and alkenes

A novel and efficient trifluoromethanesulfonic acid-catalyzed sp 3-sp2 Ci￡C bond formation reaction through the direct coupling of alcohols with alkenes has been realized under mild conditions. The present protocol provides an attractive approach to a diverse range of polysubstituted olefins in good to excellent yields with high stereo- and regioselectivities. Copyright

Calcium-catalyzed direct coupling of alcohols with organosilanes

A calcium-catalyzed direct substitution of π-activated alcohols with different organosilanes under very mild reaction conditions is presented. The high reactivity of the calcium catalyst allows efficient conversion of secondary and tertiary allylic, secondary benzylic, and tertiary propargylic alcohols with allyltrimethylsilane at room temperature. Furthermore, the first direct substitution of an alcohol with (E)- as well as (Z)-alkenylsilanes was achieved under mild reaction conditions. Copyright

Titanacyclobutenes or titanium vinyl carbene complexes? Reactivity of organotitanium species generated by the reaction of γ-chloroallyl sulfides with a titanocene(II) reagent

The reactivity of the organotitanium species generated by the reductive titanation of γ-chloroallyl sulfides with the titanocene(II) reagent [Cp2Ti{P(OEt)3}2] was studied. The organotitanium species formed from α-monosubstituted γ-chloroallyl sulfides reacted with 1,5-diphenylpentan-3-one and styrene to produce conjugated dienes and vinyl cyclopropanes as major products, thus suggesting the formation of vinyl carbene complexes as intermediates. On the contrary, the organotitanium species generated from acyclic β,γ-disubstituted γ-chloroallyl sulfides revealed titanacyclobutene-like reactivity, and their reaction with 1,5-diphenylpentan-3-one produced homoallyl alcohols. These organotitanium species did not react with styrene, but did react with dichlorophenylphosphine to afford phosphacyclobutenes. In the case of β-monosubstituted, γ-monosubstituted, and α,γ- disubstituted γ-chloroallyl sulfides, the organotitanium species reacted with both 1,5-diphenylpentan-3-one and styrene. The former reaction produced homoallyl alcohols and the latter gave vinyl cyclopropanes or unconjugated dienes. These results suggest that titanacyclobutenes and/or titanium vinyl carbene complexes are produced by the reductive titanation of γ-chloroallyl sulfides depending on their substitution patterns.

A NOVEL CARBON-CARBON BOND FORMATION BY THE LEWIS ACID CATALYZED REACTION OF β-STYRYLSILANE WITH ACETAL

Treatment of (E)- and (Z)-β-styryltrimethylsilanes with benzaldehyde diethyl acetal in the presence of Lewis acid affords selectively 1,3,5-triphenyl-(E,E)- and (E,Z)-1,4-pentadienes, respectively.