50552-26-6

Upstream product

• 250358-84-0 (Z)-3-Phenylpent-2-en-4-in-1-ol 
• 136050-77-6 2-phenyl-3,4-pentdien-2-ol 
• 84735-55-7 2,2-bis(methylthio)-4-phenyl-2,5-dihydrofuran 
• 84735-60-4 2-(methylthio)-4-phenylfuran 
• 13636-88-9 3,3-bis(methylthio)-1-phenylprop-2-en-1-one 
• 131692-90-5 (Z)-3-iodo-3-phenylprop-2-en-1-ol 
• 84735-61-5 2-methyl-5-(methylthio)-3-phenylfuran 

Relevant academic research and scientific papers

Water-Mediated Catalytic Decarboxylation Enabled Polysubstituted Furans and Allylic Alcohols with Exclusive (E)-Configurations

A water-mediated catalytic decarboxylation process toward the formation of polysubstituted furans and (E)-allylic alcohols has been reported. This protocol features wide functional group tolerance, easy operation, and only CO2-byproduct generation. These reactions can be performed on a large scale open to air under extremely ambient conditions. A range of control experiments revealed the crucial role of the water for the successful conversions as well as the origin of the chemoselectivity and exclusive stereoselectivity.

Cycloisomerization of Conjugated Allenones into Furans under Mild Conditions Catalyzed by Ligandless Au Nanoparticles

Au nanoparticles supported on TiO2 (1 mol %) catalyze the quantitative cycloisomerization of conjugated allenones into furans under very mild conditions. The reaction rate is accelerated by adding acetic acid (1 equiv), but the acid does not participate in the protodeauration step as in the corresponding Au(III)-catalyzed transformation. The process is purely heterogeneous, allowing thus the recycling and reuse of the catalyst effectively in several runs.

A general and efficient synthesis of substituted furans and dihydrofurans via gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols

A highly efficient Au-catalyzed cyclization of (Z)-enynols that proceeds under mild reaction conditions has been developed. This methodology provides rapid access to substituted furans and stereodefined (Z)-5-ylidene-2,5-dihydrofurans in a regioselective

A general and facile synthesis of substituted furans by palladium- catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols

A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 °C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.

Tungsten η1-five-membered oxygenated heterocycles derived from tungsten η1-propargyl compounds: Systematic syntheses, structural rearrangement, electrophilic alkylations, and oxidative demetalations

In the presence of BF3?Et2O, tungsten η1-propargyl complexes reacted smoothly with aldehydes to give tungsten η1-2,5-dihydro-3-furyl complexes 1-3. Treatment of 1-3 with Ph3CBF4 in CH2Cl2 (-60°C, 1 h) delivered tungsten η1-3-furylidene complexes 4-6 which underwent skeletal rearrangement to η1-furylidene 13-15 isomers when warmed to 5°C. Treatment of 4-6 with Et3N at -60°C produced tungsten η1-3-furyl complexes 7-9 which were isomerized to η1-2-furyl isomers 10-12 by a strong Bronsted acid. Protonation of 10-12 by CF3CO2H yielded η1-2-furylidene complexes 13-15. The two exceptional isomerizations were examined by in situ 1H NMR studies. Further oxidation of η1-2-furyl compounds 10-12 with m-chloroperbenzoic acid gave tungsten η1-Δ3-butenolides 16-18. Tungsten η1-3-furyl complexes 7 and 9 underwent alkylation with trimethoxymethane and aldehydes at -60°C to yield η1-3-furylidene cationic precipitates that were subsequently reduced with NaBH3CN to yield complex η1-2,5-dihydro-3-furyl compounds in good diastereoselectivity; the stereochemical courses were distinct for 7 and 9. Tungsten η1-2,5-dihydro-3-furyl, η1-2-furyl, η1-3-furyl, and η1-Δ3-butenolide complexes were decomplexed with appropriate reagents to liberate 2,5-dihydrofurans, furans, and Δ3- and Δ2-butenolides in reasonable yields.

Reactions of α-Oxo Ketene Dithioacetals with Dimethylsulfonium Methylide: A New Versatile Synthesis of Furans and Butenolides

The reaction of 1-mono- and 1,2-disubstituted 3,3-bis(methylthio)-2-propen-1-ones 1 with dimethylsulfonium methylide (2) affords 2,2-bis(methylthio)-2,5-dihydrofurans 3 via epoxide 8 which can be isolated in a special case.A couple of methods including acid treatment effected the conversion of 3 to 2-(methylthio)furans 4, which are found to be useful synthons of a variety of furans and butenolides.Two naturally occurring furans, perillene and rosefuran, were synthesized by this method.

A New Simple Synthesis of Variously Substituted Furans and Butenolides

The reaction of 1,2-disubstituted 3,3-bis(methylthio)prop-2-en-1-ones with dimethylsulfonium methylide gave 2,2-bis(methylthio)-2,5-dihydrofurans, useful synthons for a variety of furans and butenolides.