6933-35-3

Upstream product

• 188290-36-0 thiophene 
• 933-88-0 ortho-toluoyl chloride 
• 118-90-1 ortho-methylbenzoic acid 
• 53271-49-1 2-methylthiobenzoic acid S-p-tolyl ester 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 3437-95-4 2-Iodothiophene 
• 201230-82-2 carbon monoxide 
• 16419-60-6 2-Methylphenylboronic acid 
• 527-72-0 2-thiophenylcarboxylic acid 
• 10050-08-5 tri-o-tolylbismuth 
• 98-03-3 thiophene-2-carbaldehyde 

Downstream Products

• 46496-80-4 2-(thiophene-2-carbonyl)-benzoic acid 
• 356553-57-6 (2-methylphenyl)-(thiophen-2-yl)methanol 

Relevant academic research and scientific papers

One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling

A palladium-catalyzed one-pot procedure for the synthesis of aryl ketones has been developed. Triazine esters when coupled with aryl boronic acids provided aryl ketones in moderate to excellent yields (up to 95%) in the presence of 1 mol % Pd(PPh3)2Cl2 for 30 min. (Chemical Equation Presented).

Phosphine-Free, Heterogeneous Palladium-Catalyzed Atom-Efficient Carbonylative Cross-Coupling of Triarylbismuths with Aryl Iodides: Synthesis of Biaryl Ketones

A novel and highly efficient heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl iodides with triarylbismuths has been developed that proceeds smoothly at atmospheric CO pressure and provides a general and powerful tool for the preparation of various valuable biaryl ketones with high atom economy, good to excellent yield, and recyclability of the catalyst. The reaction is the first example of Pd-catalyzed carbonylative cross-coupling for the construction of biaryl ketones using triarylbismuths as substrates.

TFAA/H3PO4-Mediated C-2 acylation of thiophene: A direct synthesis of known and novel thiophene derivatives of pharmacological interest

A number of aliphatic and aromatic carboxylic acids were reacted with thiophene in the presence of trifluoroacetic anhydride and H3PO 4 to give a variety of acylated thiophenes in good to excellent yields. The methodology was used to prepare known nonsteroidal anti-inflammatory drug-based novel compounds of potential pharmacological significances. Molecular modeling studies were carried out by using nonsteroidal anti-inflammatory drug-based thiophene derivatives to assess their cyclooxygenase inhibiting potential in silico. On the basis of docking studies followed by subsequent in vitro assay, indomethacin-based thiophene derivative was identified as a novel cyclooxygenase-2 inhibitor with balanced selectivity.

A simple, efficient, and recyclable phosphine-free catalytic system for carbonylative suzuki coupling reaction of aryl and heteroaryl iodides

The carbonylative Suzuki cross-coupling reaction of arylboronic acid with aryl and heteroaryl iodides using polymer supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as an efficient heterogeneous, recyclable catalyst is described. The developed catalytic system is found to be effective for the carbonylative coupling reaction of aryl, heteroaryl, and bicyclic heteroaryl iodides (5-iodoindole and 3-iodoquinoline) with various arylboronic acid derivatives providing good to excellent yields of the desired products. The protocol is advantageous due to the ease in handling of the catalyst and simple workup procedure, and environmentally benign with effective catalyst recyclability. Georg Thieme Verlag Stuttgart - New York.

Pd/C: An efficient, heterogeneous and reusable catalyst for phosphane-free carbonylative suzuki coupling reactions of aryl and heteroaryl iodides

The carbonylative Suzuki coupling reaction of aryl boronic acid with different aryl and heteroaryl iodides was carried out to synthesize various unsymmetrical biaryl ketones by using Pd/C as an efficient, heterogeneous and reusable catalyst. The catalyst exhibits remarkable activity, and its reusability was tested up to four consecutive cycles. The reaction is applicable for various aryl and heteroaryl iodides having different steric and electronic properties. It provides good to excellent yield of the desired products. The developed protocol is advantageous with regard to the ease in handling the catalyst and the simple work-up procedure; it is also an environmentally benign process with effective catalyst recyclability. A facile protocol has been developed for the carbonylative Suzuki coupling reaction of aryl and heteroaryl iodides with Pd/C as effective, heterogeneous, reusable catalyst. The system is applicable for a wide variety of aryl and heteroaryl iodides. Copyright

Sterically hindered benzophenones via rhodium-catalyzed oxidative arylation of aldehydes

(Chemical Equation Presented) Efficient cross-coupling, allowing a straightforward access to congested benzophenones, between aromatic aldehydes and potassium aryltrifluoroborates, is described in the presence of a rhodium/tri-tert-butylphosphane catalyst system and acetone as cosolvent. The use of the stable phosphonium salts of tri-tert-butylphosphane prevented the use of highly oxidizable tri-tert-butylphosphane and allowed a careful control of the stoichiometry with the rhodium.

Novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. A structure-activity relationship investigation

1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles (DAMNIs) is a novel family of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) active at submicromolar concentration. Replacement of one phenyl ring of 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole (4) with heterocyclic rings, such as 2-thienyl or 3-pyridinyl, led to novel DAMNIs with increased activity. In HIV-1 WT cell-based assay the racemic 1-{2-[α-(thiophen-2-yl) phenylmethoxy]ethyl}-2-methyl-5-nitroimidazole (7) (EC50 = 0.03 μM) proved 5 times more active than compound 4. Docking experiments showed that the introduction of a chiral center would not affect the binding of both (R)-7 and (S)-7. The internal scoring function of the Autodock program calculated the same inhibition constant (Ki = 7.9 nM) for the two enantiomers. Compounds 7 (ID50 = 8.25 μM) were found more active than efavirenz (ID50 = 25 μM) against the viral RT carrying the K103N mutation, suggesting for these compounds a potential use in efavirenz based anti-AIDS regimens.

Ketone synthesis under neutral conditions. Cu(I) diphenylphosphinate-mediated, palladium-catalyzed coupling of thiol esters and organostannanes

(Matrix presented) A versatile approach to ketone synthesis is described. The reaction relies on the palladium-catalyzed, copper diphenylphosphinate-mediated coupling of thiol esters with organostannanes under neutral reaction conditions. This reaction complements the previously described coupling of thiol esters with boronic acids that used dual thiophilic-borophilic activation methodology.

2-(Trifluoromethylsulfonyloxy)pyridine as a Reagent for the Ketone Synthesis from Carboxylic Acids and Aromatic Hydrocarbons

A new reagent 2-(trifluoromethylsulfonyloxy)pyridine (TFOP) was prepared by the reaction of sodium salt of 2-pyridinol with trifluoromethylsulfonyl chloride in dioxane.The conpound TFOP in trifluoroacetic acid has been found to intermolecularly dehydrate from benzoic acid and aromatic hydrocarbons to give the corresponding benzophenones in high yield.It was further elucidated, in the reaction of fluorene, that a variety of carboxylic acids can be used as the acyl precursor for the aromatic ketone synthesis in conjunction with the TFOP/TFA system.This acylation procedure has been applied to the synthesis of 2-acylthiophenes, which are hard to prepare in a satisfactory yield by the classical Friedel-Crafts reaction using aluminum chloride as the catalyst.