33008-48-9

Upstream product

• 698-27-1 4-methylsalicylaldehyde 
• 4755-72-0 Chloro-phenyl-acetic acid 
• 100-39-0 benzyl bromide 
• 1135146-48-3 C₁₈H₂₂O₂Si 
• 1312936-60-9 C₁₇H₁₄O₂ 
• 100-58-3 phenylmagnesium bromide 
• 56280-66-1 diethyl(phenyl)aluminium 
• 37167-62-7 bromo-phenyl-acetic acid methyl ester 
• 108-86-1 bromobenzene 
• 108-39-4 3-methyl-phenol 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 68138-53-4 6-methyl-4-oxo-2-phenyl-4,5,6,7-tetrahydrobenzofuran 
• 53389-98-3 2-(benzyloxy)-5-methylsalicylaldehyde 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 

Downstream Products

• 53348-89-3 6-Bromomethyl-2-phenyl-benzofuran 
• 33008-42-3 1-(2-hydroxy-4-methylphenyl)-2-phenylethane-1,2-dione 
• 33008-47-8 C₃₀H₂₂O₆ 
• 33008-44-5 methyl 2-(benzoyloxy)-4-methylbenzoate 
• 33008-46-7 C₃₀H₂₆O₆ 
• 33008-43-4 1,2-Bis-(2-hydroxy-4-methyl-phenyl)-ethane-1,2-dione 
• 33008-41-2 4-methyl-bibenzyl-2-ol 

Relevant academic research and scientific papers

Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents

A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Synthesis and biological evaluation of 2-arylbenzofuran derivatives as potential anti-Alzheimer’s disease agents

Alzheimer's disease (AD) is a type of progressive dementia caused by degeneration of the nervous system. A single target drug usually does not work well. Therefore, multi-target drugs are designed and developed so that one drug can specifically bind to mu

Method for synthesizing 2-aryl benzofuran and derivatives thereof

The invention relates to a method for synthesizing 2-aryl benzofuran and derivatives thereof. According to the method, cheap and easily available 2, 3-dihydrobenzofuran compounds, an organic boron reagent and bromo-aromatic hydrocarbon are taken as raw materials, and a two-step cascade reaction is carried out under mild conditions, so that the 2-aryl benzofuran product can be conveniently prepared. At present, the reported synthesis methods of 2-aryl benzofuran and derivatives thereof mainly have the problems of long synthesis route, expensive raw materials, harsh reaction conditions and the like. Compared with reported methods, the synthesis method has the advantages of specific reaction selectivity, short reaction route and the like, and a convenient and efficient synthesis strategy is provided for laboratory preparation or industrial production of 2-arylbenzofuran products.

Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: From alkynes to benzo[b]furans and benzo[b]thiophenes

An efficient copper-promoted hydration reaction and its application in the synthesis of benzo[b ] furan and benzo[ b ] thiophene derivatives is presented starting from readily available 2-fluorophenylacetylene derivatives. The key annulation step involves

Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[ b ]furans

Benzo[b]furans were prepared in one pot based on the addition/palladium- catalyzed C-H bond functionalization of phenols with bromoalkynes. The addition reactions of phenols to bromoalkynes generated (Z)-2-bromovinyl phenyl ethers in high yields with excellent regio- and stereoselectivity. The obtained (Z)-2-bromovinyl phenyl ethers subsequently proceeded by intramolecular cyclization to afford 2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C-H bond functionalizations. It is important to note that the transformation of phenols with bromoalkynes into benzo[b]furans could be carried out in one pot with a simple and efficient tandem procedure.

The pyridyldiisopropylsilyl group: A masked functionality and directing group for monoselective ortho-Acyloxylation and ortho-Halogenation reactions of arenes

A novel, easily removable and modifiable silicon-tethered pyridyldiisopropylsilyl directing group for C-H functionalizations of arenes has been developed. The installation of the pyridyldiisopropylsilyl group can efficiently be achieved via two complementary routes using easily available 2-(diisopropylsilyl)pyridine (5). The first strategy features a nucleophilic hydride substitution at the silicon atom in 5 with aryllithium reagents generated in situ from the corresponding aryl bromides or iodides. The second milder route exploits a highly efficient room-temperature rhodium(I)-catalyzed cross-coupling reaction between 5 and aryl iodides. The latter approach can be applied to the preparation of a wide range of pyridyldiisopropylsilyl- substituted arenes possessing a variety of functional groups, including those incompatible with organometallic reagents. The pyridyldiisopropylsilyl directing group allows for a highly efficient, regioselective palladium(II)-catalyzed mono-ortho-acyloxylation and ortho-halogenation of various aromatic compounds. Most importantly, the silicon-tethered directing group in both acyloxylated and halogenated products can easily be removed or efficiently converted into an array of other valuable functionalities. These transformations include protio-, deuterio-, halo-, boro-, and alkynyldesilylations, as well as a conversion of the directing group into the hydroxy functionality. In addition, the construction of aryl-aryl bonds via the Hiyama-Denmark cross-coupling reaction is feasible for the acetoxylated products. Moreover, the ortho-halogenated pyridyldiisopropylsilylarenes, bearing both nucleophilic pyridyldiisopropylsilyl and electrophilic aryl halide moieties, represent synthetically attractive 1,2-ambiphiles. A unique reactivity of these ambiphiles has been demonstrated in efficient syntheses of arylenediyne and benzosilole derivatives, as well as in a facile generation of benzyne. In addition, preliminary mechanistic studies of the acyloxylation and halogenation reactions have been performed. A trinuclear palladacycle intermediate has been isolated from a stoichiometric reaction between diisopropyl(phenyl)pyrid-2-ylsilane (3a) and palladium acetate. Furthermore, both C-H functionalization reactions exhibited equally high values of the intramolecular primary kinetic isotope effect (kH/k D=6.7). Based on these observations, a general mechanism involving the formation of a palladacycle via a C-H activation process as the rate-determining step has been proposed.

Benzofurans prepared by C-H bond functionalization with acylsilanes

(Chemical Equation Presented) Instant carbenes - that's hot: The thermal 1,2-Brook rearrangement of acylsilanes generates siloxycarbene intermediates that can undergo intramolecular C-H bond insertion to provide benzofuran derivatives. This metal-free tan

Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: Short synthesis of natural 2-arylbenzofurans

A new synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic or acyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP system is found to be the most effective for constructing various benzofurans. Synthetic utility of this reaction is demonstrated by the short synthesis of natural benzofurans without protection of the hydroxy group. The synthesis of Stemofuran A was accomplished via condensation of ketones with aryloxyamine and subsequent reaction with TFAT-DMAP in a four-step synthesis with 72% overall yield. Similarly, Eupomatenoid 6 and Coumestan were synthesized through the reaction of oxime ether with TFAT-DMAP. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Novel and selective palladium-catalyzed annulations of 2-alkynylphenols to form 2-substituted 3-halobenzo[b]furans

A novel and selective palladium-catalyzed annulation of 2-alkynylphenols method for the synthesis of 2-substituted 3-halobenzo[b]furans is presented. In the presence of PdX2, CuX2, and HEt3NX, 2-substituted 3-halobenzo[b]f

A copper-free Sonogashira reaction using a Pd/MgLa mixed oxide

A new Pd/MgLa mixed oxide is found to be an efficient catalyst for the Sonogashira reaction of aryl iodides, bromides and even activated chlorides in the absence of a copper salt.