30717-57-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 5151, 1988 DOI: 10.1021/jo00256a048Tetrahedron Letters, 23, p. 3255, 1982 DOI: 10.1016/S0040-4039(00)87584-X

Upstream product

• 83575-72-8 Dimethylamino-thiophen-2-yl-trimethylsilanyloxy-acetonitrile 
• 88-15-3 2-Acetylthiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 105-45-3 acetoacetic acid methyl ester 
• 273928-11-3 2-[Tris(dimethylamino)methyl]-thiophen 
• 1003-09-4 2-bromothiophene 
• 479486-96-9 N,N-dimethyl (trimethylsilyl)methanamide 
• 98-03-3 thiophene-2-carbaldehyde 
• 139224-74-1 2-(thiophen-2-yl)-2-((trimethylsilyl)oxy)acetonitrile 
• 67-56-1 methanol 
• 636-72-6 2-thiophenemethanol 
• 527-72-0 2-thiophenylcarboxylic acid 
• 20893-30-5 2-cyanomethylthiophene 
• 27757-85-3 2-Aminomethylthiophene 

Downstream Products

• 150906-85-7 2-(Cyclopenta-2,4-dienylidene-phenyl-methyl)-thiophene 
• 1244039-09-5 N,N-dimethyl-5-(perfluorophenyl)thiophene-2-carboxamide 
• 1003-31-2 thiophene-2-carbonitrile 
• 1361405-12-0 N,N-dimethyl-5-(2,3,5,6-tetrafluoro-4'-methoxy-[1,1'-biphenyl]-4-yl)thiophene-2-carboxamide 
• 1430206-00-0 C₁₇H₂₂BrNOS₂ 
• 214493-03-5 5,5’-dibromo-4,4’-dihexyl-2,2’-bithiophene 
• 83495-30-1 5,5′-diphenyl-2,2′-bithiophene 
• 1430206-24-8 C₁₇H₁₅NOS₂ 
• 1430206-26-0 C₁₉H₁₅NOS₂ 
• 115257-02-8 5,5'-bis(phenylethynyl)-2,2'-dithiophene 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 26019-17-0 2-(dimethylaminomethyl)thiophene 
• 6846-13-5 N-phenyl-2-thiophenecarboxamide 
• 636-72-6 2-thiophenemethanol 

Relevant academic research and scientific papers

Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines

Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.

Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals

We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.

Structure–Activity Relationships of 1-Benzoylazulenes at the OX1 and OX2 Orexin Receptors

We previously demonstrated the potential of di- or trisubstituted azulenes as ligands (potentiators, weak agonists, and antagonists) of the orexin receptors. In this study we investigated 27 1-benzoylazulene derivatives, uncovering seven potentiators of t

Facile Access to Amides from Oxygenated or Unsaturated Organic Compounds by Metal Oxide Nanocatalysts Derived from Single-Source Molecular Precursors

Oxidative amidation is a valuable process for the transformation of oxygenated organic compounds to valuable amides. However, the reaction is severely limited by the use of an expensive catalyst and limited substrate scope. To circumvent these limitations, designing a transition-metal-based nanocatalyst via more straightforward and economical methodology with superior catalytic performances with broad substrate scope is desirable. To resolve the aforementioned issues, we report a facile method for the synthesis of nanocatalysts NiO and CuO by the sol-gel-assisted thermal decomposition of complexes [Ni(hep-H)(H2O)4]SO4 (SSMP-1) and [Cu(μ-hep)(BA)]2 (SSMP-2) [hep-H = 2-(2-hydroxylethyl)pyridine; BA = benzoic acid] as single-source molecular precursors (SSMPs) for the oxidative amidation of benzyl alcohol, benzaldehyde, and BA by using N,N-dimethylformamide (DMF) as the solvent and as an amine source, in the presence of tert-butylhydroperoxide (TBHP) as the oxidant, at T = 80 °C. In addition to nanocatalysts NiO and CuO, our previously reported Co/CoO nanocatalyst (CoNC), derived from the complex [CoII(hep-H)(H2O)4]SO4 (A) as an SSMP, was also explored for the aforementioned reaction. Also, we have carefully investigated the difference in the catalytic performance of Co-, Ni-, and Cu-based nanoparticles synthesized from the SSMP for the conversion of various oxygenated and unsaturated organic compounds to their respective amides. Among all, CuO showed an optimum catalytic performance for the oxidative amidation of various oxygenated and unsaturated organic compounds with a broad reaction scope. Finally, CuO can be recovered unaltered and reused for several (six times) recycles without any loss in catalytic activity.

Nickel-catalyzed aminocarbonylation of aryl halides using carbamoylsilane as an amide source

The nickel-catalyzed aminocarbonylation of aryl halides using carbamoylsilane as an amide source is developed. The procedure can prepare both tertiary and secondary amides, and is applicable to various carbamoylsilanes and aryl halides containing differen

Heterogeneous recyclable nano-palladium catalyzed amidation of esters using formamides as amine sources

Catalyzed by supported palladium nanoparticles, a decarbonylative amidation reaction between various aryl esters and formamides by C-O bond activation has been developed for the synthesis of amides. The catalyst can be reused and shows high activity after

A use of the carboxamides aryl carbonyl aminolysis method of preparing amide

The invention discloses a method for preparing amides via a decarbonylation ammonolysis reaction of aryl ester and formamide. The method comprises the following steps: dissolving a palladium catalyst, aryl ester and formamide in a solvent, and stirring fo

General and efficient oxidative amidation of benzyl alcohols with amines using diacetoxyiodobenzene and TBHP

A facile oxidative coupling of alcohols and amines to construct amides was developed using DIB as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. Various secondary and tertiary amides were prepared in good yield utilizing inexpensive and readily available reagents under mild reaction condition. The reaction involved operational simplicity, metal free oxidation, and wide functional group tolerance as attractive features.

Oxidative coupling of methylamine with an aminyl radical: Direct amidation catalyzed by I2/TBHP with HCl

Oxidative coupling of methylamines with an aminyl radical to construct amides was developed in the presence of an I2/TBHP catalyst under acidic conditions via the two cleavages of the sp3 C-N bond of aryl-methylamines and the sp2 C-N bond of N-substituted formamides respectively. This transition-metal-free protocol provides a novel synthetic tool for the construction of N-substituted amides and a series of arylamides can be easily obtained with good yields. This journal is the Partner Organisations 2014.

Copper-catalyzed formation of N,N-dimethyl benzamide from nitrile and DMF under an O2 atmosphere

Amidation of nitrile with N,N-dimethylformamide (DMF) was catalyzed by Cu2O with 1,10-phenanthroline as a ligand under an oxygen atmosphere. A variety of N,N-dimethyl benzamides were obtained in yields up to 84%.