256439-83-5

Upstream product

• 271-89-6 1-benzofurane 
• 292638-85-8 acrylic acid methyl ester 
• 4265-16-1 2-formylbenzo[b]furan 
• 1117-71-1 methyl-4-bromo-2-butenoate 
• 90-02-8 salicylaldehyde 
• 85614-50-2 1-(benzofuran-2-yl)butan-1-one 
• 96-32-2 bromoacetic acid methyl ester 
• 28809-07-6 methyl (E)-4-(2-formylphenoxy)but-2-enoate 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 5927-18-4 trimethyl phosphonoacetate 

Downstream Products

• 477250-32-1 N-(-α-Methylbenzyl)-3-Amino-3-(Benzo[d]furan-2-yl)propionic Acid Methyl Ester 
• 1373037-80-9 (S)-3-(3-(benzofuran-2-yl)propanoyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 1373038-08-4 C₂₄H₂₂F₃NO₄ 
• 1373038-18-6 C₂₄H₂₂F₃NO₄ 
• 21683-86-3 3-(Benzofuran-2-yl)propionic acid 

Relevant academic research and scientific papers

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Efficient synthesis of acrylates bearing an aryl or heteroaryl moiety: One-pot method from aromatics and heteroaromatics using formylation and the horner-wadsworth-emmons reaction

Acrylates bearing an aryl or heteroaryl moiety were efficiently prepared by a one-pot process employing a sequence of lithiation, formylation and the Horner-Wadsworth-Emmons reaction starting from aromatic and heteroaromatic compounds. This method can efficiently introduce an acrylate moiety into aromatic and heteroaromatic compounds.

Phosphetane oxides as redox cycling catalysts in the catalytic wittig reaction at room temperature

Recently, phosphorus redox cycling has gained significant importance for a number of transformations originally requiring the use of stoichiometric amounts of phosphorus reagents. While these methodologies have several benefits, high catalyst loadings (≥10 mol percent) and harsh reaction conditions (T ≥ 100 °C) often limit their versatility and applicability. Herein, we report differently substituted phosphetane oxides as efficient catalysts for the catalytic Wittig reaction. The phosphetane scaffold is easy to modify, and a number of catalysts can be obtained in a simple two-step synthesis. The activity in the Wittig reaction significantly surpasses previously reported phospholane-based catalysts and the reaction can be conducted with catalyst loadings as low as 1.0 mol percent even at room temperature. Furthermore, a Br?nsted acid additive is no longer required to achieve high yields at these mild conditions. A methyl-substituted phosphetane oxide was employed to synthesize 25 different alkenes with yields of up to 97percent. The methodology has a good functional group tolerance and the reaction can be performed starting with alkyl chlorides, bromides, or iodides. Additionally, it was possible to use poly(methylhydrosiloxane) as the terminal reductant in the catalytic Wittig reaction employing 2-MeTHF as a renewable solvent. The intermediates of the Wittig reaction were analyzed by 31P NMR spectroscopy, and in situ NMR experiments confirmed phosphane oxide as the resting state of the catalyst. Further kinetic investigations revealed a striking influence of the base on the rate of phosphane oxide reduction.

4-Aryl Pyrrolidines as a Novel Class of Orally Efficacious Antimalarial Agents. Part 1: Evaluation of 4-Aryl- N-benzylpyrrolidine-3-carboxamides

Identification of novel chemotypes with antimalarial efficacy is imperative to combat the rise of Plasmodium species resistant to current antimalarial drugs. We have used a hybrid target-phenotype approach to identify and evaluate novel chemotypes for malaria. In our search for drug-like aspartic protease inhibitors in publicly available phenotypic antimalarial databases, we identified GNF-Pf-4691, a 4-aryl-N-benzylpyrrolidine-3-carboxamide, as having a structure reminiscent of known inhibitors of aspartic proteases. Extensive profiling of the two terminal aryl rings revealed a structure-activity relationship in which relatively few substituents are tolerated at the benzylic position, but the 3-aryl position tolerates a range of hydrophobic groups and some heterocycles. Out of this effort, we identified (+)-54b (CWHM-1008) as a lead compound. 54b has EC50 values of 46 and 21 nM against drug-sensitive Plasmodium falciparum 3D7 and drug-resistant Dd2 strains, respectively. Furthermore, 54b has a long half-life in mice (4.4 h) and is orally efficacious in a mouse model of malaria (qd; ED99 ～ 30 mg/kg/day). Thus, the 4-aryl-N-benzylpyrrolidine-3-carboxamide chemotype is a promising novel chemotype for malaria drug discovery.

Scope and Limitation of the Microwave-Assisted Catalytic Wittig Reaction

We have developed a microwave-assisted catalytic Wittig reaction. In this paper, we give full account of the scope and limitations of this reaction. A screening of various commercially available phosphine oxides as precatalysts revealed Bu3P=O to be the most promising candidate. We tested 10 silanes for the in situ reduction of the phosphine oxide to generate Bu3P as the actual catalyst. Different epoxides were tested as masked bases. In this context, cyclohexene oxide as well as butylene oxide proved to be suitable. The reaction could be carried out at 125 C, but higher yields and E/Z selectivities were obtained at 150 °C. Under the optimised reaction conditions, more than 40 examples for the conversion of various aldehydes into the corresponding alkenes are reported. The products were obtained in yields of up to 88 with high E selectivities. Moreover, we also describe the further screening of several chiral phosphines as catalysts for the microwave-assisted enantioselective catalytic Wittig reaction. The scope and limitations of the microwave-assisted catalytic Wittig reaction have been evaluated with respect to the catalyst, silane, solvent, reaction conditions, and substrates.

A convenient synthesis of 2-substituted benzofurans from salicylaldehydes

Base-mediated cyclocondensation of 2-hydroxybenzaldehydes with 3-bromo-1-(arylsulfonyl)propenes and 4-bromocrotonates afforded (E)-2-(2-sulfonylvinyl)benzofurans and (E)-2-benzofuranyl-3-acrylates respectively.

First Microwave-Assisted Catalytic Wittig Reaction

We introduce a novel catalytic Wittig reaction based on an inexpensive and readily available phosphane oxide as a precatalyst. The performance of the reaction under microwave irradiation led to significantly improved yields and reaction rates relative to those obtained under conventional heating. Moreover, herein we enclose the first example of the asymmetric catalytic Wittig reaction based on a chiral phosphane as the catalyst.

Versatile palladium-catalyzed C-H olefination of (hetero)arenes at room temperature

The room-temperature oxidative C-H/C-H cross-couplings between (hetero)arenes and alkenes, coumarins or quinones have been reported by using a highly electrophilic palladium species [Pd(TFA)2], generated in situ from Pd(OAc)2and TFA, as the catalyst and cheap (NH4)2S2O8as the oxidant under air.

Insight into the role of the counteranion of an imidazolium salt in organocatalysis: A combined experimental and computational study

N-Heterocyclic carbenes (NHCs) can serve as very reactive nucleophilic catalysts and exhibit strong basicity. Herein, we initiate a combined experimental and computational investigation of the NHC-catalyzed ring-closing reactions of 4-(2-formylphenoxy)but