68727-84-4

Upstream product

• 591-50-4 iodobenzene 
• 72601-11-7 4-hydroxy-4-methyl-pent-2-ynoic acid ethyl ester 
• 201230-82-2 carbon monoxide 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 611-73-4 Benzoylformic acid 
• 115-11-7 isobutene 
• 536-74-3 phenylacetylene 
• 61423-02-7 ethyl 1,1-dimethyl-3-phenylpropargyl acetate 
• 75-65-0 tert-butyl alcohol 

Relevant academic research and scientific papers

Carbonylation of Tertiary Propargylic Alcohols Catalyzed by a Cationic Palladium(II) Complex: Synthesis of 2(5H)-Furanones

Tertiary propargylic alcohols reacted with carbon monoxide in the presence of catalytic quantities of a cationic palladium(II) complex, (BF4)2, to afford 2(5H)-furanones and/or 2,3-dienoic acids, the precursor of the furanones, in good

Butenolide synthesis from functionalized cyclopropenones

A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst loadings. Importantly, the cyclization is tolerant of a broad range of functional groups, yielding a variety of α- and γ-substituted butenolides.

Esters as Radical Acceptors: β-NHC-Borylalkenyl Radicals Induce Lactonization by C?C Bond Formation/Cleavage on Esters

Substituted propargyl acetates are converted into 4-boryl-2(5H)-furanones upon thermolysis in the presence of an N-heterocyclic carbene borane (NHC-borane) and di-tert-butyl peroxide. The acetyl methyl group is lost during the reaction as methane. Evidence suggests that the reaction proceeds by a sequence of radical events including: 1) addition of an NHC-boryl radical to the triple bond; 2) cyclization of the resultant β-borylalkenyl radical to the ester carbonyl group; 3) β-scission of the so-formed alkoxy radical to provide the 4-boryl-2(5H)-furanone and a methyl radical; and 4) hydrogen abstraction from the NHC-borane to return the initial NHC-boryl radical and methane.

A α, β - unsaturated butyrolactone synthetic method

The invention discloses a synthetic method of alpha,beta-unsaturated butyrolactone. Synthetic route of the synthetic method is represented by a formula in the invention, wherein R1 is used for representing aryl group or tertiary butyl, R2 is used for representing alkyl group or hydrogen, and R3 and R4 are both used for representing one randomly selected from aryl group and alkyl group. Raw materials used in the whole reaction process are cheap and easily available, so that reaction cost is reduced greatly; substrate application range of the synthetic method is wide; operation of the whole reaction is simple and convenient; and yield is higher than 80%.

Palladium-Catalyzed Cyclocarbonylation of Terminal and Internal Alkynols to 2(5H)-Furanones

A series of substituted alkynols, containing alkyl, phenyl, and vinyl groups at the acetylenic terminal, were found to undergo direct carbonylation to the corresponding substituted 2(5H)-furanones in 67-98% yield. This reaction requires catalytic quantiti

A new synthetic route to α-hydroxy butyrolactones

α-Oxocarboxylic acids react with olefins under acid conditions to give α-hydroxy butyrolactones (3-hydroxy-2-oxotetrahydrofurans) which can be readily dehydrated to give α,β-unsaturated butyrolactones 2-oxo-2,5-dihydrofurans.

THE MUKAIYAMA REACTION OF KETENE BIS(TRIMETHYLSILYL)ACETALS WITH α-HALO ACETALS - A CONVENIENT BUTENOLIDE SYNTHESIS

Ketene bis(trimethylsilyl) acetals were reacted with α-halo acetals giving β-alkoxy-γ-halo acids which were converted to butenolides by reaction with equivalents of base.This constitutes a novel and short butenolide synthesis.

THE PALLADIUM -TRIBUTYL FORMATE REAGENT IN THE STEREOSELECTIVE HYDROGENATION, AND STEREO- AND REGIOSELECTIVE HYDROARYLATION OF ALKYL 4-HYDROXY-2-ALKYNOATES: A ROUTE TO SUBSTITUTED BUTENOLIDES

The reaction of aryl iodides with alkyl 4-hydroxy-2-alkynoates in the presence of formic acid, tri-n-butylamine and a palladium(II) catalyst provides a convenient route to functionalized substituted butenolides through a one pot hydroarylation/cyclization reaction.In the presence of formic acid, tri-n-butylamine and a palladium(II) catalyst, alkyl 4-hydroxy-2-alkynoates undergo a one pot hydrogenation/cyclization reaction to the butenolide ring.By increasing the excess of formic acid, direct formation of saturated γ-lactones can be observed.Reaction occur with high stereoselectivity and, in the case of the hydroarylation, with goog regioselectivity.