39517-87-8

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 116-09-6 hydroxy-2-propanone 
• 1463-04-3 (3-methylbut-3-en-1-ynyl)benzene 
• 4440-01-1 lithium phenylacetylide 
• 536-74-3 phenylacetylene 
• 53343-13-8 1-hydroxypropan-2-one tetrahydropyran ether 
• 7647-01-0 hydrogenchloride 
• 7065-27-2 2-methyl-2-(2-phenylethynyl)oxirane 

Downstream Products

• 39517-83-4 4-methyl-2-phenylfuran 
• 317845-71-9 4-methyl-4-phenylethynyl-[1,3]dioxolan-2-one 
• 1221575-72-9 methyl 4-methyl-2-phenylfuran-3-carboxylate 
• 104092-51-5 4-methyl-2-phenyl-3-mercury(II)-chloride-furane 
• 317845-79-7 Methyl 5-hydroxy-4-methyl-2-phenylpenta-2,3-dienoate 

Relevant academic research and scientific papers

C-Quaternary alkynyl glycinols via the Ritter reaction of cobalt complexed alkynyl glycols

A novel approach to C-quaternary alkynyl glycinols based on the Ritter reaction of acetonitrile with cobalt complexed alkynyl glycols is presented. The reaction is promoted by acids such as H2SO4 or BF3·Et2O to give oxazolines as the reaction products. These are subjected to cobalt complex cleavage in oxidative conditions and subsequent acidic hydrolysis providing amino alcohols. The substrates for the Ritter reaction can be easily assembled to introduce structural diversity at both variable positions. The Ritter reaction conditions for oxazoline formation is compatible with a range of substituents at the alkyne terminal position providing oxazolines in moderate to good yields. Methyl, hydroxymethyl and silyloxymethyl substituents at the reaction center of glycols are well tolerated, while a phenyl group in this position is detrimental to the reaction. s

Poly(ethylene glycol) as a reaction matrix in platinum- or gold-catalyzed cycloisomerization: A mechanistic investigation

Design for diversity: A new catalytic system based on PEG-3400 and a metal salt (Pt or Au) was designed to efficiently perform a cycloisomerization reaction under microwave irradiation, which gave diverse heterocycles in good to excellent yields, after a

Synthesis of furan-3-carboxylic and 4-methylene-4,5-dihydrofuran-3- carboxylic esters by direct palladium iodide catalyzed oxidative carbonylation of 3-yne-1,2-diol derivatives

A variety of 3-yne-1,2-diol derivatives 1, bearing a primary or secondary alcoholic group at C-1, have been efficiently converted into high value added furan-3-carboxylic esters 2 in one step by PdI2/KI-catalyzed direct oxidative carbonylation, carried out in alcoholic media under relatively mild conditions (100 °C under 40 atm of a 4/1 mixture of CO and air). Carbonylated furans 2 were obtained in fair to excellent isolated yields (56-93%) through a sequential 5-endo-dig heterocyclization-alkoxycarbonylation- dehydration process, using only oxygen as the external oxidant. Under similar conditions, 2-methyl-3-yne-1,2-diols 3, bearing a tertiary alcoholic group, afforded 4-methylene-4,5-dihydrofuran-3-carboxylates 4 in satisfactory yields (58-70%).

A simple and convenient synthesis of substituted furans and pyrroles by CuCl2-catalyzed heterocyclodehydration of 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols

A simple and economical synthesis of substituted furans and pyrroles, by ligand-free CuCl2-catalyzed heterocyclodehydration of readily available 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols, respectively, is presented. Reactions are carried out in MeOH at 80-100 °C for 1-24 h and afford the corresponding heterocyclic derivatives in 53-99% isolated yields.

Expedient syntheses of β-iodofurans by 5-endo-dig cyclisations

5-endo-dig cyclisations of 3-alkyne-1,2-diols using iodine as the electrophile proceed smoothly to deliver excellent yields of the corresponding β-iodofurans. The necessary precursors are available from a number of different approaches, notably regioselec

Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclisations of 3-alkyne-1,2-diols

Iodocyclisations of 3-alkyne-1,2-diols, obtained from acetylides and α-hydroxy-ketones or esters, give generally excellent yields of β-iodofurans by 5-endo-dig cyclisation followed by dehydration.

Synthesis of δ-lactones from 2-alkynyl epoxides and 4-alkynyl-1,3-dioxolan-2-ones by palladium catalysed carbonylation and conjugate nucleophilic addition

Synthesis of δ-lactones from 2-alkynyl epoxides and 4-alkynyl-1,3-dioxolan-2-ones by palladium catalysed carbonylation and conjugate nucleophilic addition was investigated. The stereocontrolled conjugate addition of nucleophiles to the electron deficient

Asymmetric dihydroxylation of enynes

Catalytic asymmetric dihydroxylations of 1,3-enynes were studied using 9-0-(9′-phenanthryl) dihydroquinidine (PHN-DHQD) 1 and 1,4-bis-(9-0-dihydroquinidine) phthalazine (DHQD2-PHAL) 2. Terminal olefins showed moderate (38-79% ee) and trans-disu

PREPARATION OF FURANS FROM ALKYNOLS UTILIZING PALLADIUM CATALYZED INTRAMOLECULAR ADDITION OF ALCOHOL TO ACETYLENE AS A KEY REACTION

A procedure is described for the synthesis of furans from 3-alkyn-1,2-diols or 2-methoxy-3-alkyn-1-ols by palladium catalyzed intramolecular addition of alcoholic moiety to acetylene linkage followed by elimination of water or methanol.The intermediary 3-furylpalladiums can be trapped with allyl halides affording 3-allylfurans in good yields.