4265-14-9

Upstream product

• 103-82-2 phenylacetic acid 
• 292081-10-8 [2-(bis-phenylsulfanyl-methyl)-phenoxy]-tert-butyl-dimethyl-silane 
• 95-48-7 ortho-cresol 
• 103-80-0 phenylacetyl chloride 
• 54008-77-4 2-bromo-1-benzofuran 
• 100-39-0 benzyl bromide 
• 62360-00-3 (Z)-2-fluoro-3-phenylprop-2-enyl acetate 
• 108-95-2 phenol 
• 98437-24-2 benzofuran-2-boronic acid 
• 100-51-6 benzyl alcohol 
• 1276042-67-1 (2-phenylacetoxybenzyl)triphenylphosphonium bromide 
• 1301768-66-0 2-(bromomethyl)phenyl phenylacetate 
• 18268-10-5 salicylaldehyde diphenyl dithioacetal 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 77071-96-6 3-acetyl-2-benzylbenzofuran 
• 13524-66-8 2-benzyldihydrobenzofuran 
• 27052-21-7 (benzofuran-2-yl)phenylmethanol 
• 6272-40-8 2-benzoylbenzofuran 
• 1418311-41-7 2-(methoxy(phenyl)methyl)benzofuran 
• 440633-77-2 2-(2-benzylbenzo[b]furan-3-yl)acetonitrile 

Relevant academic research and scientific papers

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

The palladium-catalyzed synthesis of indole/benzofurancontaining diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

Sterically Demanding AgI and CuI N-Heterocyclic Carbene Complexes: Synthesis, Structures, Steric Parameters, and Catalytic Activity

The synthesis and full characterization of new air-stable AgI and CuI complexes bearing structurally bulky expanded-ring N-heterocyclic carbene (erNHC) ligands is presented. The condensation of protonated NHC salts with Ag2/sub

Construction of Di(hetero)arylmethanes Through Pd-Catalyzed Direct Dehydroxylative Cross-Coupling of Benzylic Alcohols and Aryl Boronic Acids Mediated by Sulfuryl Fluoride (SO2F2)

A practical Pd-catalyzed direct dehydroxylative coupling of (hetero)benzylic alcohols with (hetero)arylboronic acids for the constructions of di(hetero)arylmethane derivatives under SO2F2 was described. This new method provided a strategically distinct approach to di(hetero)arylmethane derivatives from readily available and abundant benzylic alcohols under mild condition.

Dearomative Dienolate-Mediated Catalysis: A Remote Activation Strategy for Asymmetric Functionalization of Benzylic C-H Bonds of Heteroaryl Aldehydes

A dearomative remote activation strategy for the asymmetric functionalization of benzylic C-H bonds of heteroaryl aldehydes under bifunctional Br?nsted base catalysis has been developed. The in situ generated o-QDMs-type dienolate intermediates were effic

Palladium-catalyzed intermolecular coupling of 2-haloallylic acetates with simple phenols, and sequential formation of benzofuran derivatives through the intramolecular cyclization

We accomplished the synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed reaction of 2-haloallylic acetates with simple phenols in the presence of a base. The reaction proceeded through the intermolecular attack of the nucleophile on the central carbon atom of the π-allyl group, carbon-halogen bond cleavage, and sequential intramolecular cyclization.

Palladium-catalyzed intermolecular coupling of 3-substituted propargylic carbonates with phenols: Synthesis of 2-substituted benzofuran derivatives

We accomplished the synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed reaction of 3-substituted propargylic carbonates with phenols. The 2-substituted benzofuran derivatives were obtained through the intermolecular coupling of t

Synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed intermolecular coupling of 2-fluoroallylic acetates with phenols

We investigated the intermolecular coupling reaction of 2-fluoroallylic acetates with simple phenols by the [Pd(C3H5)Cl]2, DPPF, and KHMDS at 100?°C for 16?h, and succeeded in obtaining 2-substituted benzofuran derivatives

Impregnated Copper(II) Oxide on Magnetite as Catalyst for the Synthesis of Benzo[b]furans from 2-Hydroxyarylcarbonyl Derivatives and Alkynes

The coupling-allenylation-cyclization reaction sequence of o-hydroxybenzaldehydes with alkynes in the presence of 4-methylbenzenesulfonohydrazide was carried out in ethanol as a nontoxic biorenewable solvent and in the presence of impregnated copper(II) oxide on magnetite as a heterogeneous catalyst. The catalyst can be easily removed from the reaction medium by a simple magnetic decantation, and the reaction can be performed with a very low copper loading. The in situ reduction of the starting copper(II) oxide nanoparticles into copper(0) sheets made the recyclability of catalyst impossible. The versatility of the reaction was shown by employing different o-hydroxyacetophenones to give 2,3-disubstituted benzo[b]furans. The reaction can be carried out on a gram scale without any complications.

Syntheses of 2-Benzylbenzofuran Derivatives and 2-Aryl-nitrochroman Derivatives from Nitroalkene Precursors

Simple and straightforward methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described. Benzofurans were generated from nitroalkenes by reduction with NaBH4 followed by a Nef reaction and acid-mediated cyclization, whereas 3-substituted 2-benzylbenzofurans were prepared from nitroalkenes by reactions with Grignard reagents followed by a Nef reaction and an acid-mediated cyclization in a one-pot process. The synthesis of chromans involved a Knoevenagel condensation and the 1,4-diazabicyclo[2.2.2]octane (DABCO) assisted cyclization of β-(2-hydroxyphenyl)-nitroethanes and benzaldehydes, also in a one-pot process. Simple and convenient methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described.

Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts

Enantioselective hydrogenation of furans and benzofurans remains a challenging task. We report the hydrogenation of 2- and 3-substituted furans by using iridium catalysts that bear bicyclic pyridine-phosphinite ligands. Excellent enantioselectivities and high conversions were obtained for monosubstituted furans with a 3-alkyl or 3-aryl group. Furans substituted at the 2-position and 2,4-disubstituted furans proved to be more difficult substrates. The best results (80-97% conversion, 65-82% enantiomeric excess) were obtained with monosubstituted 2-alkylfurans and 2-[4-(trifluoromethyl)phenyl]furan. Benzofurans with an alkyl substituent at the 2- or 3-position also gave high conversions and enantioselectivity, whereas 2-aryl derivatives showed essentially no reactivity. The asymmetric hydrogenation of a 3-methylbenzofuran derivative was used as a key step in the formal total synthesis of the cytotoxic naphthoquinone natural product (-)-thespesone.