74528-46-4

Upstream product

• 5703-57-1 3-phenylpent-4-enoic acid 
• 6049-50-9 4-Oxo-3-phenylpentanoic acid 
• 63795-90-4 3-phenyl-4-oxopentanoic acid ethyl ester 
• 124513-11-7 1-methylphenacyl (trimethylsilyl)acetate 
• 95904-83-9 4-methyl-3-phenylcyclobut-2-en-1-one 
• 108-86-1 bromobenzene 
• 36781-65-4 pent-3-ynoic acid 
• 591-50-4 iodobenzene 
• 87841-05-2 5-Methylen-4-phenyl-2(5H)-furanon 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 536-74-3 phenylacetylene 
• 5650-40-8 2-hydroxypropiophenone 
• 1094064-55-7 ((C₆H₅)3P)AuC₄O₂(CH₃)(H)(H) 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Catalytic Cross-Coupling of Vinyl Golds with Diazonium Salts under Photoredox and Thermal Conditions

Catalytically generated vinyl gold complexes from tert-butyl allenoates were found to undergo an efficient cross-coupling with arenediazonium salts. The gold(I)-gold(III) redox cycle can be accessed under two different conditions, i.e., visible-light photoredox as well as a thermally induced radical chain pathway. The current C(sp2)-C(sp2) cross-coupling protocol that is catalytic in gold, would make available desirable structural diversity to the traditional cross-coupling chemistry.

Gold-catalyzed cascade oxidative cyclization and arylation of allenoates

An AuI/AuIII catalytic system was found to be effective for the cascade oxidative arylation and cyclization of allenoates with arylboronic acids to give the corresponding cyclic adducts in moderate yields. This reaction system constitutes a new method for the synthesis of β-aryl-γ-butenolides under mild conditions. Based on the previous mechanistic studies, a proposed AuI/AuIII redox catalytic cycle has been outlined. An AuI/AuIII catalytic system was found to be effective for the cascade oxidative arylation and cyclization of allenoates with various arylboronic acids to give the corresponding cyclic adducts in moderate yields. This reaction system enabled the synthesis β-aryl-γ-butenolides under mild conditions. Based on previous mechanistic studies, an AuI/AuIII redox catalytic cycle has been outlined. Copyright

Cu(I)-catalyzed oxidative cyclization of alkynyl oxiranes and oxetanes

In the presence of a Cu(I) catalyst and a pyridine oxide, alkynyl oxiranes and oxetanes can be converted into functionalized five- or six-membered α,β-unsaturated lactones or dihydrofuranaldehydes. This new oxidative cyclization is proposed to proceed via an unusual allenyloxypyridinium intermediate.

FURANONE COMPOUNDS AND LACTAM ANALOGUES THEREOF

The present invention provides a compound of formula I and a compound of formula II, methods of use and formulations thereof.

Butenolide annelation using a manganese(III) oxidation. A synthesis of 4-arylfuran-2(5H)-ones

A general procedure was developed for the annelation of a butenolide to an aromatic ketone that highlighted a manganese(III) oxidation of aromatic ketones. The oxidation of aromatic ketones with manganese(III) acetate in the presence of 2-bromoacetic acid or the Mn(II) salt of this carboxylic acid provided a regioselectively convenient synthesis of 2-(2-bromoacetoxy) ketones. An Arbuzov or Wittig reaction of 2-(2-bromoacetoxy) ketones followed by cyclisation furnished 4-arylfuran-2(5H)-ones in good yield.

Selective palladium-mediated synthesis of racemic 4,5-disubstituted 5H- furan-2-ones from 3-ynoic acids and organic halides

Racemic 4,5-disubstitued 5H-furan-2-ones have been selectively Synthesized by addition of 1,21.6 equiv of aryl, alkenyl or 1-alkynyl halides and catalytic mounts of Pd(OAc)2 and a soft ligand such as tri-2- furylphosphine or triphenylarsine to

VICINAL ALKYLATION OF ALKYNES. A SHORT ROUTE TOWARD Δα,β BUTENOLIDES, FURANS AND CYCLOPENTENONES.

Cyclobutenones 1 which are readily prepared from alkynes and keteniminium salts 2 were regiospecifically converted into Δα,β butenolides 4 or cyclopentenones 7.Reaction of 4 with diisobutylaluminium hydride yielded the corresponding substituted

Synthesis of 4-Penten-4-olides (γ-Methylene-γ-butyrolactones) via 4-Pentenoic Acids

4-Penten-4-olides (γ-Methylene-γ-butyrolactones) 7 are easily accessible starting from allylic alcohols 1, which on ortho ester Claisen rearrangement and hydrolytic work-up furnish 4-pentenoic acids 5.The latter on iodolactonization and hydrogen iodide elimination by means of 1,8-diazabicycloundec-7-ene (DBU) furnish 7, in good over-all yield and with variable substitution patterns. - Iodolactonization under kinetic control shows moderate 1,2- or 1,3-asymmetric induction (3:1 and ca. 2:1, respectively).The composition of the iodolactone mixtures 6 as well as the individual relative configurations are deduced from 1H and 13C NMR data. - Similary, the spirobipentenolide 13 is obtained starting from diethyl diallylmalonate (9) via 11 resulting from ester iodocyclization.

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.