34721-89-6

Upstream product

• 99853-91-5 4-chloro-1-phenyl-pent-3-en-1-one 
• 108-24-7 acetic anhydride 
• 583-05-1 1-phenylpentane-1,4-dione 
• 534-22-5 2-methylfuran 
• 62-53-3 aniline 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 119305-57-6 1,1-dimethoxy-2-trimethylsiloxypropane 
• 54930-80-2 2-methyl-3-(methylthio)-5-phenylfuran 
• 119582-54-6 3-methoxy-1-phenyl-4-trimethylsiloxy-1-pentanone 
• 100-52-7 benzaldehyde 
• 74-86-2 acetylene 
• 80569-10-4 1-Phenyl-2-penten-1,4-dion-4-dimethylhydrazon 
• 117993-84-7 2,3-dihydro-2-methoxy-5-methyl-2-phenylfuran 
• 136022-09-8 α-<1-(Methylsulfinyl)but-2-ynyl>benzenemethanol 

Downstream Products

• 3810-26-2 3-phenyl-2-cyclopenten-1-one 
• 4457-59-4 tetrahydro-2-methyl-5-phenylfuran 
• 76160-71-9 3-(5-methyl-3-phenyl-1,4,2-dioxazol-5-yl)acrylophenone 
• 76160-72-0 4a,7a-dihydro-7a-methyl-3,6-diphenylfuro<3,2-e>-1,4-2-dioxazine 
• 5069-26-1 2-methyl-5-phenylthiophene 
• 19842-61-6 2-methyl-5-phenyl-selenophene 
• 17265-50-8 5-Benzoyl-3-methylisothiazole 
• 40941-31-9 2-(bromomethyl)-5-phenylfuran 
• 1255392-53-0 1,4-epoxy-4-methyl-1-phenyl-1,4-dihydronaphthalene 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Metal catalysed rearrangement of cyclopropanespiro-β-lactones to 2-furanones

The rearrangement of 5-oxo-4-oxaspiro[2.3]hexanes (cyclopropanespiro-β-lactones) to 2(5H)-furanones and 2(3H)-furanones is shown to be a general reaction which is promoted by metal catalysts. A mechanism is proposed, involving the novel insertion of a metal species into the O-C(β) bond of the β-lactone ring, which explains the basic features of the reaction, including its regioselectivity.

Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles

An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles.

Gold-Catalyzed Tandem Oxidative Coupling Reaction between β-Ketoallenes and Electron-Rich Arenes to 2-Furylmethylarenes

A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl3 and phenyliodine diacetate. The AuIII salt catalyzed the cyclization of β-ketoallenes to form a 2-furylmethyl gold intermediate, and the subsequent C-H functionalization of arenes proceeded smoothly. During the oxidative coupling, nucleophilic additions occurred at the center and terminal carbon atoms of the allene moiety to form C-O and C-C bonds.

Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes

A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient.

Direct (Hetero)arylation of Heteroarenes Catalyzed by Unsymmetrical Pd-PEPPSI-NHC Complexes under Mild Conditions

With the aim of developing a facile and efficient method to access structurally intriguing and valuable functionalized (hetero)aryls, two unsymmetrical Pd-PEPPSI-type NHC complexes (PEPPSI, pyridine-enhanced precatalyst preparation, stabilization, and initiation; NHC, N-heterocyclic carbene) were designed and synthesized to catalyze the direct arylation of heteroarenes with (hetero)aryl bromides. The results demonstrated that the utilization of this "unsymmetrical"strategy led to much higher efficiency in comparison to the commonly used C2-symmetric Pd-PEPPSI-type NHC complexes. Furthermore, a broad range of heteroaromatics and (hetero)aryl bromide partners with a wide variety of functional groups were all amenable to the developed protocol even at as low as 0.05 mol % catalyst loading and under aerobic conditions. More importantly, along with our study, we also found that the present protocol could provide expedient access to the gram-scale synthesis of the muscle relaxant drug dantrolene and conjugated mesopolymers.

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.

Studies towards iodine-catalyzed dehydrative-cycloisomerization of pent-4-yne-1,2-diols to di- and tri-substituted furans

An efficient and single-step iodine catalyzed and metal-free synthesis of di and tri-substituted 2-methylfuran derivatives were achieved from 1-popargyl-1,2-diols. Stereospecific synthesis of starting 1,2-diols was achieved by indium mediated Barbier type

Method for synthesizing substituted furan

Provided is a method for synthesizing substituted furan. Iodohydrocarbon and terminal propargyl alcohol produce Sonogashira coupling reaction to generate an intermediate product 3-alkyne-1-alcohol, then isomeric cyclization occurs under the effect of Dess

Rh-Catalyzed Reactions of 3-Diazoindolin-2-imines: Synthesis of Pyridoindoles and Tetrahydrofuropyrroloindoles

The rhodium-catalyzed reactions of 3-diazoindolin-2-imines with furans and dihydrofuran furnished 9H-pyrido[2,3-b]indoles and tetrahydrofuro[3′,2′:4,5]pyrrolo[2,3-b]indoles, respectively. A cascade reaction mechanism involving an α-imino rhodium carbene i

Asymmetric hydrogenation of disubstituted furans

An enantioselective hydrogenation of disubstituted furans has been developed by using a chiral ruthenium catalyst with N-heterocyclic carbene ligands. This reaction converts furans into valuable enantioenriched disubstituted tetrahydrofurans.