84132-74-1

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 5780-90-5 (4-Methoxyphenyl)mercuric acetate 
• 70744-47-7 (p-methoxyphenyl)tri-n-butylstannane 
• 696-62-8 para-iodoanisole 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 141339-54-0 bis(4-anisyl)iodonium triflate 
• 115298-63-0 phenyl(4-methoxyphenyl)iodonium triflate 
• 123-11-5 4-methoxy-benzaldehyde 
• 51410-44-7 1-(4-methoxylphenyl)-2-propen-1-ol 
• 309723-10-2 1-(1-allyloxyallyl)-4-methoxybenzene 
• 18649-43-9 4-methoxyphenyllead(IV) triacetate 

Downstream Products

• 87116-54-9 (3aα,4α,6aα)-tetrahydro-4-(4-methoxy-1-phenyl)-2',2'-dimethylfuro<3,4-d>-1',3'-dioxole 
• 79623-15-7 2-p-methoxyphenyltetrahydrofuran 
• 94540-81-5 2-(4-methoxyphenyl)-5-phenylfuran 
• 1334240-34-4 methyl 2-methoxy-5-(5-(4-methoxyphenyl)furan-2-yl)benzoate 
• 1334240-33-3 2-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)furan 
• 1334240-32-2 2-(4-methoxy-3-nitrophenyl)-5-(4-methoxyphenyl)furan 
• 1230-48-4 2,5-Bis(4-methoxyphenyl)furan 
• 17113-31-4 2-(4-methoxyphenyl)furan 
• 97060-29-2 1-(4-methoxyphenyl)-but-2-en-1-one 
• 4160-51-4 1-(4-methoxyphenyl)-1-butanone 

Relevant academic research and scientific papers

Probing the mechanism of the Heck reaction with arene diazonium salts by electrospray mass and tandem mass spectrometry

Key ionic intermediates of the Heck reaction of arene diazonium salts have been intercepted and structurally characterized by ESI-MS/MS. The use of electrospray ionization enables the ionic species to be transferred smoothly to the gas phase. A catalytic cycle for this reaction involving all the Pd cationic species intercepted has been proposed (see scheme).

Palladacycle-Catalyzed Regioselective Heck Reaction Using Diaryliodonium Triflates and Aryl Iodides

We describe a P-containing palladacycle-catalyzed regioselective Heck reaction of 2,3-dihydrofuran with diaryliodonium salts and aryl iodides to afford 2-aryl-2,5-dihydrofurans and 2-aryl-2,3-dihydrofurans, respectively, in good yields. Mechanistic studie

Chemo-Enzymatic Metathesis/Aromatization Cascades for the Synthesis of Furans: Disclosing the Aromatizing Activity of Laccase/TEMPO in Oxygen-Containing Heterocycles

The unprecedented Trametes versicolor laccase/TEMPO-catalyzed aromatization of 2,5-dihydrofurans to furans is described. A variety of furan derivatives have been synthesized in moderate to high conversions (21-99%) and yields (20-76%) under mild reaction

Regioselective Heck reaction catalyzed by Pd nanoparticles immobilized on DNA-modified MWCNTs

This is the first report of regioselective Heck reaction of aryl iodides with 2,3-dihydrofuran using heterogonous nanocatalyst. Herein, palladium nanoparticles is immobilized on DNA-modified multi walled carbon nanotubes and characterized by FT-IR spectroscopy, UV-vis spectroscopy, field emission scanning electron microscopy, X-ray diffraction, transmission electron microscopy, inductively coupled plasma and elemental analysis. DNA as a well-defined structure and biodegradable natural polymer generate the palladium catalyst which showed high activity in common and regioselective Heck reaction in excellent yields and good selectivity under ligand-free and mild reaction conditions. Moreover, the catalyst could be recovered and reused at least nine times without any considerable loss of its catalytic activity.

Direct Access to Furoindolines by Palladium-Catalyzed Intermolecular Carboamination

A versatile Pd-catalyzed intermolecular syn-carboamination of dihydrofurans giving access to the ubiquitous furoindoline motif is described. The efficiency of the process relies on the use of Buchwald-type biarylphosphines and the perfect control for site-selectivity of Pd insertion across the C=C bond. A catalytic sequence consisting of Heck and carboamination cross-coupling reactions from readily available dihydrofurans affords - in usually high chemical yields and high levels of diastereocontrol - poly(hetero)cyclic compounds that would be difficult to access by established methods. Encouraging preliminary results for the enantioselective carboamination of 2,3-dihydrofurans are also disclosed.

Controlling olefin isomerization in the heck reaction with neopentyl phosphine ligands

The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.

Assisted tandem catalytic RCM-aromatization in the synthesis of pyrroles and furans

An assisted tandem catalytic transformation of diallyl amines and diallyl ethers into N-aryl pyrroles and furans, respectively, is described. The sequence relies on ring closing metathesis followed by dehydrogenation of the initially formed dihydropyrroles and dihydrofurans. Both steps are Ru-catalyzed, but the sequence requires only one precatalyst, because conversion of the metathesis catalyst into the dehydrogenation catalyst is achieved in situ, triggered by the oxidant tert-butyl hydroperoxide.

Ru- and Pd-catalysed synthesis of 2-arylfurans by one-flask heck arylation/oxidation

2,5-Disubstituted furans were synthesized by one-flask Heck arylation/oxidation sequences. The starting materials are 2-substituted 2,3-dihydrofurans, conveniently available by RCM/isomerization sequences, and arenediazonium salts. These react in ligand-free Heck reactions to afford 2,5-disubstituted 2,5-dihydrofurans, which are oxidized to the corresponding furans without isolation or intermediate workup. The oxidation is conveniently achieved with chloranil or DDQ, depending on the substrate.

The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the synthesis of flavonoids

The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu4NHSO4 as ad

Tandem olefin metathesis/hydrogenation at ambient temperature: Activation of ruthenium carbene complexes by addition of hydrides

Sodium hydride activates ruthenium carbene complexes to catalyze hydrogenation reactions subsequent to ring closing olefin metathesis. Under these conditions, hydrogenation of cyclopentenols proceeds smoothly at ambient temperature and under 1 atm of hydrogen in toluene. An alternative protocol was developed that involves the formation of hydrogen in situ by reaction of excess sodium hydride with protic functional groups and water.