127392-19-2

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 74-86-2 acetylene 
• 466686-21-5 (3E,5E)-7-acetoxy-7-phenylhepta-3,5-dien-2-one 
• 944725-17-1 (E)-2,3-dihydro-2-methoxy-5-methyl-2-(2-phenylethenyl)furan 
• 51801-01-5 (E)-1-acetoxy-1-phenyl-2-butene 
• 534-22-5 2-methylfuran 
• 100-42-5 styrene 
• 620-02-0 5-Methylfurfural 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 466686-17-9 (E)-4-oxo-1-phenylbut-2-en-1-yl acetate 

Downstream Products

• 1266556-02-8 C₁₃H₁₄O₃ 

Relevant academic research and scientific papers

Aerobic dehydrogenative Heck reactions of heterocycles with styrenes: A negative effect of metallic Co-oxidants

The aerobic dehydrogenative Heck reaction (DHR) of heterocycles with styrenes was found to be more efficient in the absence of metallic cooxidants. According to a study of the isotope effect, the C-H cleavage was the rate-determining step of the catalytic

Scope and limitations of the photooxidations of 2-(α-Hydroxyalkyl) furans: Synthesis of 2-hydroxy-exo -brevicomin

Photooxygenation of 2-(α-hydroxyalkyl)furans at 5 °C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(α,β-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.(Figure Presented)

Synthesis of dihydrofurans containing trifluoromethyl ketone and heterocycles by radical cyclization of fluorinated 1,3-dicarbonyl compounds with 2-thienyl and 2-furyl substituted alkenes

Manganese(III) acetate based radical cyclization of various fluorinated 1,3-dicarbonyl compounds with 2-thienyl and 2-furyl substituted alkenes produced 3-trifluoroacetyl and 2-trifluoromethyl-dihydrofurans in good yields. The radical cyclizations of 2-methyl-5-[(E)-2-phenylvinyl]furan 2b and 2-[(E)-2-phenylvinyl]thiophene 2c led to the formations of 5-(5-methyl-2-furyl)- 4,5-dihydrofuran and 5-(2-thienyl)-4,5-dihydrofuran, respectively. In the reactions of 1,3-dicarbonyls with alkenes, 2-thienyl substituted alkenes formed 4,5-dihydrofurans in higher yields than 2-furyl substituted alkenes.

Dehydrogenative heck reaction of furans and thiophenes with styrenes under mild conditions and influence of the oxidizing agent on the reaction rate

CiH vs. CiBr in Heck: The direct dehydrogenative coupling of furans and thiophenes with styrenes occurs under mild conditions (see scheme). This method allows the coupling of brominated substrates through CiH bond activation. In addition, DMSO and benzoquinone had a positive effect on the reaction rate.

Palladium-catalyzed dehydrogenative coupling of furans with styrenes

Under palladium(II)-catalyzed and oxidative conditions, the coupling of furans with styrenes leads to the formation of Heck-type products In medium to good yields. The reaction Is highly regio- and stereoselective, giving frans-olefins predominantly.

[4+1]/[2+1] Cycloaddition reactions of fischer carbene complexes with α,β-unsaturated ketones and aldehydes

(Chemical Equation Presented) Put two and two together: Fischer carbene complexes and α,β-unsaturated carbonyl compounds smoothly react under thermal conditions to give 2,3-dihydrofurans, and from them furans or 1,4-dicarbonyl compounds were easily accessible (see scheme). This cycloaddition process involves a cyclopropanation reaction followed by rearrangement from the acylcyclopropane to a dihydrofuran.

A novel cyclization reaction between 2,3-bis(trimethylsilyl)buta-1,3-diene and acyl chlorides with straightforward formation of polysubstituted furans

A novel cyclization process of 2,3-bis(trimethylsilyl)buta-1,3-diene with various acyl chlorides in the presence of aluminium trichloride affords 2,5-disubstituted or 2,3,5-trisubstituted furans in short reaction time; a subsequent acylation process of th

Electrocyclization reactions of 1-Aza- and 1-oxapentadienyl and -heptatrienyl cations: Synthesis of pyrrole and furan derivatives

Quantum chemical DFT calculations (B3LYP/6-31+G) have been used to gain insight into the conformational and energy properties of the 1-aza- and 1-oxapentadienyl and -heptatrienyl cations 1, 2, 3, and 4. The calculated thermodynamic and kinetic data of the ring-closure reactions giving the cyclic products 5-14 are reported and discussed with respect to the experimental results. Experimentally, synthetic routes to the α,β-unsaturated carbonyl compounds 24 and 27, each with a leaving group in the γ-position, have been developed. These compounds have been investigated with respect to their ability to undergo 1,5-electrocyclization reactions to yield 2,5-disubstituted furans 28 upon heating in the presence of acid, presumably through the intermediate formation of the 1-oxapentadienyl cations 2. From the corresponding imine 29a the pyrrole 30d was obtained after treatment with tetrakis (triphenylphosphane) palladium. In the presence of benzylamine and the Pd° catalyst, the corresponding pyrroles 30a-c were formed from 24 and 27. The homologous α,β,γ,δ-unsaturated carbonyl compounds 31 afforded 2-vinyl-substituted furans 32 upon heating with acid, and the 2-vinyl-substituted pyrroles 34 on treatment with benzylamine and the Pd catalyst. No seven-membered heterocyclic rings were formed. Surprisingly, the α,β-unsaturated carbonyl compounds with two phenyl substituents at the γ-position also provided pyrrole derivatives 40 through a formal dimerization. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

NOVEL SYNTHESIS OF ETHYNYL VINYL CARBINOLS AND 2,5-DISUBSTITUTED FURANS FROM ALDEHYDES

Gem-substituted aryl, aralkenyl and 2-furyl ethynyl vinyl carbinols as well as 2,5-disubstituted furans can be obtained by a novel addition and rearrangement reaction of acetylene with the appropriate aldehydes.