24265-92-7

Upstream product

• 24190-60-1 1-(benzyloxy)-4-(phenylethynyl)benzene 
• 100-52-7 benzaldehyde 
• 100-44-7 benzyl chloride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 89523-63-7 benzylzinc chloride 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 718-25-2 1-fluoro-4-styrylbenzene 
• 718-25-2 (E)-4-fluorostilbene 
• 100-51-6 benzyl alcohol 
• 3462-95-1 (4-fluorobenzyl)triphenylphosphonium chloride 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 100-39-0 benzyl bromide 
• 591-50-4 iodobenzene 

Relevant academic research and scientific papers

Carbonyl–Olefin Cross-Metathesis Through a Visible-Light-Induced 1,3-Diol Formation and Fragmentation Sequence

A visible-light-mediated approach to carbonyl–olefin cross-metathesis is described. Photoinduced hole catalysis was used to promote the formation of 1,3-diols from aldehydes and styrenes, which were then readily fragmented under acidic conditions to form the cross-metathesis products. The use of 1,3-diols as intermediates, rather than the energetically more demanding oxetanes, provides a new, orthogonal mechanistic strategy for carbonyl–olefin cross-metathesis. Furthermore, this approach does not require any metals, ligands, or additives, and provides the products with high levels of E selectivity. A mechanistic rationale is provided and supported by both theoretical calculations and experiments. Additionally, a practical synthesis of a new acridinium-based photocatalyst, including full characterization, is presented.

A family of stilbene-ethers as photolabile protecting groups for primary alcohols offers controlled deprotection based on choice of wavelength

A novel stilbene-ether type of photolabile protecting group (PPG) for hydroxyl group has been developed. It contains a stable aryl ether group in the protected form and can be deprotected by acid-catalyzed photorearrangement under 300-nm irradiation. The selective deprotection has also been achieved by irradiation of the mixture of 4-alkoxystilbene and 2-(4-alkoxystyryl)furan at 365 nm.

Synthesis of alkyloxy stilbenes by one-pot O-alkylation-Wittig and O-alkylation-Wittig-Heck reaction sequence

A new route for the synthesis of alkyloxy stilbenes from hydroxy benzaldehydes is developed by a combination of one-pot reactions. Tandem one-pot O-alkylation-Wittig and O-alkylation-Wittig-Heck reactions offer a simple access to conjugated alkyloxy stilbenes. A highly conjugated tetra(p-alkyloxystyryl)benzene was synthesized from 1,2,4,5-tetrabromobenzene involving a series of one-pot operations following the O-alkylation-Wittig-Heck scheme.

Cu(acac)2-catalyzed synthesis of functionalized bis(arylmethyl)zinc reagents and their olefination reaction with aromatic aldehydes

An efficient and facile copper(II) acetylacetonate catalyzed synthesis of functionalized bis(arylmethyl)zinc reagents from arylmethyl halides and their olefination reaction with aromatic aldehydes is reported. Aluminum trichloride was found to be the key ingredient in these reactions and (E)-stilbenes were obtained in high yields. Georg Thieme Verlag Stuttgart · New York.

Stereodivergent ruthenium-catalyzed transfer semihydrogenation of diaryl alkynes

[Ru3(CO)12]-catalyzed transfer semihydrogenation of various functionalized diaryl alkynes with N,N-dimethylformamide (DMF) and water as hydrogen source affords cis- and trans-stilbenes. The stereodivergent approach can be switched by the use of acetic (HOAc) or trifluoroacetic (TFA) acid as additives. The catalytic processes can be applied to the synthesis of analogues of natural products such as cis-combretastatin A-4 and trans-resveratrol. Copyright

Palladium-catalyzed stereoselective synthesis of (E)-stilbenes via organozinc reagents and carbonyl compounds

In the presence of a catalytic amount of PdCl2(PPh 3)2 and a silylating agent, organozinc halides reacted with carbonyl compounds to give the corresponding (E)-stilbenes in good to excellent yields under mild conditions. The reaction mechanism is briefly discussed.