98098-60-3

Upstream product

• 696-63-9 4-Methoxybenzenethiol 
• 100-07-2 4-methoxy-benzoyl chloride 
• 201230-82-2 carbon monoxide 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 622-29-7 N-Benzylidenemethylamine 

Downstream Products

• 7291-00-1 N,N-dimethyl-4-methoxybenzamide 
• 1388470-24-3 (4-(2-hydroxyphenyl)piperazin-1-yl)(4-methoxyphenyl)methanone 
• 19486-73-8 N-tert-butyl-4-methoxybenzamide 
• 315248-36-3 4-methoxy-N-(4-nitrobenzyl)benzamide 
• 1422008-22-7 tert-butyl N-(3-(4-methoxybenzamido)propyl)carbamate 
• 1173915-06-4 1,4-bis(4-methoxyphenylthio)-2,3,5,6-tetrafluorobenzene 
• 701-53-1 p-methoxybenzoyl fluoride 

Relevant academic research and scientific papers

Visible-Light-Mediated Cross Dehydrogenative Coupling of Thiols with Aldehydes: Metal-Free Synthesis of Thioesters at Room Temperature

Thioesters play a crucial role in biological systems and serve as important building blocks for organic synthesis. Herein, Eosin Y and TBHP mediated photochemical cross dehydrogenative coupling (PCDC) between feedstock aldehydes and thiols has been descri

Lithium-Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3-Sulfanyl-Oxetanes as Bioisosteres

3-Sulfanyl-oxetanes are presented as promising novel bioisosteric replacements for thioesters or benzyl sulfides. From oxetan-3-ols, a mild and inexpensive Li catalyst enables chemoselective C?OH activation and thiol alkylation. Oxetane sulfides are formed from various thiols providing novel motifs in new chemical space and specifically as bioisosteres for thioesters due to their similar shape and electronic properties. Under the same conditions, various π-activated secondary and tertiary alcohols are also successful. Derivatization of the oxetane sulfide linker provides further novel oxetane classes and building blocks. Comparisons of key physicochemical properties of the oxetane compounds to selected carbonyl and methylene analogues indicate that these motifs are suitable for incorporation into drug discovery efforts.

Palladium-catalyzed thiocarbonylation of aryl, vinyl, and benzyl bromides

(Chemical Equation Presented) A catalytic protocol for synthesis of thioesters from aryl, vinyl, and benzyl bromides as well as benzyl chlorides was developed using only stoichiometric amounts of carbon monoxide, produced from a solid CO precursor inside a two-chamber system. As a catalytic system, the combination of bis(benzonitrile) palladium(II) chloride and Xantphos furnished the highest yields of the desired compounds, along with the weak base, NaOAc, in anisole at 120°C. The choice of catalytic system as well as solvent turned out to be important in order to ensure a high chemoselectivity in the reaction. Both electron-rich and electron-deficient aryl bromides worked well in this reaction. Addition of 1 equiv of sodium iodide to the reaction improved the chemoselectivity with the electron-deficient aryl bromides. The thiol scope included both aryl and alkyl thiols, including 2-mercaptobenzophenones, whereby a thiocarbonylation followed by a subsequent McMurry coupling yielded differently substituted benzothiophenes. It was demonstrated that the methodology could be applied for 13C introduction into the thiophene ring.

Polymer supported Pd catalyzed thioester synthesis via carbonylation of aryl halides under phosphine free conditions

A new polymer supported phosphine free Pd(ii) complex has been synthesized and characterized. The catalytic performance of the complex has been tested for the carbonylation of aryl halides into aryl thioesters under mild reaction conditions. Thioesters were obtained in excellent yields from various aryl iodides and thiols in the presence of carbon monoxide and polymer supported palladium catalyst. The effects of solvent, base, reaction time and catalyst amount for the thioester synthesis were reported. This catalyst showed excellent catalytic activity and recyclability. The polymer supported Pd(ii) catalyst could be easily recovered by filtration and reused more than five times without appreciable loss of its initial activity.

Pd-catalyzed thiocarbonylation with stoichiometric carbon monoxide: Scope and applications

A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)2 and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.

CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers

Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.

An alternative approach towards the syntheses of thioethers and thioesters using CsF-Celite in acetonitrile

It has been found that syntheses of thioethers and thioesters of aliphatic, aromatic and heterocyclic compounds, bearing thiol groups, can be accomplished with alkyl, acyl, benzyl or benzoyl halides in acetonitrile and cesium fluoride-Celite. In this manner, compounds like ethanethiol, 1-pentanethiol, thiophenol, 4-methoxythiophenol, 4-nitrothiophenol, and 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, and 2-mercapto-2-thiazoline can be successfully alkylated, acylated, benzylated or benzoylated. This procedure is convenient, efficient and practical for the preparation of thioethers and thioesters.

Cobalt carbonyl catalyzed reaction of mercaptans with Schiff bases and carbon monoxide

Thiophenols and p-methylbenzyl mercaptan react with Schiff bases and carbon monoxide in benzene, in the presence of cobalt carbonyl, to give amides as the pricipal products.These amides arise from cleavage of the carbon-nitrogen double bond of the reactant imine.The reaction is applicable to a variety of Schiff bases (i.e. aliphatic, benzylic, aromatic).Thioesters and olefins are usually obtained as reaction by-products.

COBALT CARBONYL CATALYZED REACTIONS OF DISULFIDES: CARBONYLATION TO THIOESTERS AND DESULFURIZATION TO SULFIDES.

Aromatic and benzylic disulfides react with carbon monoxide and a catalytic amount of cobalt carbonyl to give thioesters and carbonyl sulfide, while the presence of t-butyl peroxide results in the formation of sulfides in high yields.