1575-47-9

Upstream product

• 2243-35-8 2-acetoxyacetophenone 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 91767-65-6 2-chloro-3-hydroxy-3-phenyl-butyric acid ethyl ester 
• 2016-01-5 ethyl 3-phenyl-3-formylpropanoate 
• 36122-35-7 2-phenylmaleic anhydride 
• 78920-11-3 4-phenyl-5-hydroxy-2-(5H)-furanone 
• 591-50-4 iodobenzene 
• 57061-30-0 4-Phenylsulfanylfuran-2(5H)-one 
• 3461-50-5 methyl trans-3-methylcinnamate 
• 100-34-5 benzene diazonium chloride 
• 497-23-4 2-buten-4-olide 
• 84735-60-4 2-(methylthio)-4-phenylfuran 
• 103675-22-5 (Z)-3-Phenyl-4-(tetrahydro-pyran-2-yloxy)-but-2-enoic acid methyl ester 
• 74796-60-4 (E)-4-Phenyl-2-trimethylsilanyloxy-pent-3-enenitrile 

Downstream Products

• 28784-56-7 3,6a-diphenyl-6,6a-dihydro-3aH-furo[3,4-d]isoxazol-4-one 
• 1008-73-7 4-phenyldihydrofuran-2(3H)-one 
• 78920-21-5 5-phenylpyridazin-3(2H)-one 
• 99558-31-3 4,5-dihydro-5-phenylpyridazin-3(2H)-one 
• 99389-53-4 (E)-4-Hydroxy-3-phenyl-but-2-enoic acid 
• 13679-41-9 3-phenylfuran 
• 1575-55-9 5-bromo-4-phenyl-2(5H)-furanone 
• 1008-73-7 (R)-4-phenyl-4,5-dihydrofuran-2(3H)-one 
• 68844-05-3 4-phenyldihydrofuran-2-one 
• 103647-10-5 4-Methoxy-3-phenyl-2-butenoic acid lactone 
• 147030-98-6 1-(4-phenylfuran-2-yl)ethanone 
• 40951-19-7 sodium 4-hydroxy-3-phenylbutanoate 
• 99558-42-6 5-phenyltetrahydropyridazin-3(2H)-one 
• 1381783-44-3 3-diazo-4-phenyl-dihydrofuran-2-one 

Relevant academic research and scientific papers

Palladium-catalyzed cross-coupling reactions of 4-tosyl-2(5H)-furanone with boronic acids: A facile and efficient route to generate 4-substituted 2(5H)-furanones

An efficient and facile synthesis of 4-substituted 2(5H)-furanones using palladium catalyzed cross-coupling reactions between 4-tosyl-2(5H)-furanone and boronic acids is reported herein.

Highly regio- and stereoselective palladium-catalyzed allene bifunctionalization cascade via π-allyl intermediate

We report a palladium-catalyzed allene bifunctionalization reaction that forms C–C and either C–O or C–N bonds in one pot with excellent regio- and stereoselectivity. Carboxylic acids, amides, and hydroxide are all suitable nucleophiles. Organoboronic acid acts as hydroxide transfer reagent. An intermediate π-allyl palladium complex was isolated, which yields improved catalytic performance as well as evidence of the origin of stereoselectivity. A derivatization study emphasizes the utility of the functionalized allylic products.

Palladium-Catalyzed Cross-Coupling of Alkenyl Carboxylates

Carboxylate esters have many desirable features as electrophiles for catalytic cross-coupling: they are easy to access, robust during multistep synthesis, and mass-efficient in coupling reactions. Alkenyl carboxylates, a class of readily prepared non-aromatic electrophiles, remain difficult to functionalize through cross-coupling. We demonstrate that Pd catalysis is effective for coupling electron-deficient alkenyl carboxylates with arylboronic acids in the absence of base or oxidants. Furthermore, these reactions can proceed by two distinct mechanisms for C?O bond activation. A Pd0/II catalytic cycle is viable when using a Pd0 precatalyst, with turnover-limiting C?O oxidative addition; however, an alternative pathway that involves alkene carbopalladation and β-carboxyl elimination is proposed for PdII precatalysts. This work provides a clear path toward engaging myriad oxygen-based electrophiles in Pd-catalyzed cross-coupling.

A Rubrolide synthetic method of compound (by machine translation)

The invention discloses a Rubrolide synthetic method of compound, comprises the following steps: (1) under the action of the phosphate, substituted phenylacetaldehydes and chloroacetic acid obtained through the reaction of intermediate 1; (2) the intermediate 1 with NaBH4 Reduction reaction, reduction reaction product is then purged acid dehydration reaction to obtain the intermediate 2; (3) under the action of alkali, the intermediate 2 and substituted benzene formaldehyde reflux reaction to obtain the target product. The present invention provides synthetic method of compound Rubrolide using substituted phenylacetaldehydes, glyoxalic acid, phosphoric acid, NaBH4 And concentrated sulfuric acid as the raw materials, raw materials are cheap, easy to obtain, the synthetic method is simple, mild reaction, compared with the traditional synthetic method, not only to avoid expensive raw materials and a noble metal catalyst, greatly reduces the production cost, and also avoids the harsh reaction conditions; and the mild reaction conditions, the operation is simple, friendly to the environment, the solvent is easily recovered, is suitable for industrial production. (by machine translation)

Substituted aryl methyl radical Rubrolide compound and its preparation method and application

The invention discloses a substituted aryl methyl radical Rubrolide compound, its structure is shown as formula I: Wherein R is phenyl, pyridyl, pyrimidinyl, furyl, pyrazolyl, thiazolyl or thienyl, the R is one or more of the substituent of the substituted, the substituted the base is mutual independent, and is selected from one or more saturated or unsaturated alkyl, alkoxy, halogen, fluorine-containing methyl, nitro, cyano, ester or amide. The present invention provides substituted aryl-methyl radical Rubrolide compound of novel structure, which has a broad spectrum of herbicidal activity, can be used for various crops weed control. The invention also provides the preparation method and application.

Palladium-catalyzed hydrodehalogenation of butenolides: An efficient and sustainable access to β-arylbutenolides

Several α-unsubstituted β-arylbutenolides have been prepared in 69–92% yield by reductive dehalogenation of α-halo-β-arylbutenolides. The latter were assembled in a single-step from α,β-dihalobutenolides, which are accessible on a large-scale from biomass-derived furfural. Our dehalogenation protocol is illustrated by a new synthesis of the marine antibiotics rubrolide E and F, and 3″-bromorubrolide F.

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf) 2, which is in situ prepared from PhI(OAc) 2 and Me 3 SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5 H)-ones or furan-2(3 H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

Hg/Pt-catalyzed conversion of bromo alkynamines/alkynols to saturated and unsaturated γ-butyrolactams/lactones via intramolecular electrophilic cyclization

Convenient and general Hg(ii)/Pt(iv) catalyzed syntheses of γ-butyrolactams and α,β-unsaturated γ-butyrolactones/lactams are described via intramolecular electrophilic cyclizations of bromoalkynes with tosylamino and hydroxyl tethers. The reaction features the use of wet solvents, the exclusion of any base and additive, mild conditions and practical yields. We also synthesised few chiral lactams through this pathway. Additionally, it is shown that the NHTs group distanced further from the homopropargylic position assists regioselective bromoalkyne hydration to yield useful α-bromoketones. Furthermore, Boc protected bromo homo propargyl amines undergo 6-endo-dig cyclization through Boc oxygen to give bromomethylene substituted oxazinones.

Highly Efficient Catalytic Formation of (Z)-1,4-But-2-ene Diols Using Water as a Nucleophile

The first general catalytic and highly stereoselective formation of (Z)-1,4-but-2-ene diols is described from readily available and modular vinyl-substituted cyclic carbonate precursors using water as a nucleophilic reagent. These 1,4-diol scaffolds can be generally prepared in high yields and with ample scope in reaction partners using a simple synthetic method that does not require the presence of any additive or any special precaution unlike the stoichiometric approaches reported to date. Control experiments support the mechanistic view that hyperconjugation within the catalytic intermediate after decarboxylation plays an imperative role to control the stereoselective outcome of these reactions.

Handy Protocols using Vinyl Nosylates in Suzuki-Miyaura Cross-Coupling Reactions

Vinyl nosylates derived from 1,3-dicarbonyl compounds could be engaged in Suzuki-Myaura cross coupling reactions with aryl-, vinyl- and methylboronic acids or trifluoborate derivatives at room temperature in the presence of 2mol% of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) [PdCl2(dppf)]. One-pot procedures have been set up for practical and efficient nosylation-cross-coupling reactions. Nosylate, as a cheap novel pseudo-halide, gives very stable compounds and is very efficient in Suzuki-Myaura cross coupling reactions (21 examples, 44-99%).