53573-34-5

Upstream product

• 100-53-8 phenylmethanethiol 
• 75-98-9 Trimethylacetic acid 
• 75908-55-3 3-(benzylthio)-1,2-benzisothiazole 1,1-dioxide 
• 3282-30-2 pivaloyl chloride 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 201230-82-2 carbon monoxide 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Relevant academic research and scientific papers

Microwave-assisted direct thioesterification of carboxylic acids

A one-pot synthesis of thioesters directly from carboxylic acids, N,N′-diphenylthiourea, triethylamine, and primary alkyl halides is described. Microwave-assisted heating and a catalytic amount of 4- (dimethylamino)pyridine (DMAP) further improved the yields. Both aromatic and aliphatic carboxylic acids were converted to the corresponding thioesters, and many functional groups were compatible with this reaction. Several possible reaction intermediates were investigated, and the quaternary ammonium salts, derived from alkyl halides and tertiary amines, were the intermediates to yield thioesters. A new reaction mechanism for this thioesterification is proposed.

A simple acylation of thiols with anhydrides

Different thiols were efficiently acylated at room temperature with different anhydrides in the presence of potassium carbonate. Chemoselective protection of thiol in the presence of hydroxy group was achieved using di-tert-butyl dicarbonate and isatoic anhydride.

A novel approach for the direct conversion of alkylsulfonyl derivatives into alkylcarbonyl derivatives via tin-free radical carbonylation

A novel radical approach for the direct conversion of RSO2X into RCOX in a single step is devised; the present approach is very simple, highly efficient, and minimizes formation of by-product. The Royal Society of Chemistry.

Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species

(Chemical Equation Presented) Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride-MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-α-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O2-CBu t)2 between pivalic anhydride and MoO2Cl 2 as the catalyst.

An Odorless Preparative Method of Sulfides and Thiocarboxylic S-Esters Using 3-(Alkylthio)-1,2-benzisothiazole 1,1-Dioxide

It was found that sodium salt of 1,2-benzisothiazole-3(2H)-thione 1,1-dioxide (thiosaccharin) readily reacted with alkyl halide affording 3-(alkylthio)-1,2-benzisothiazole 1,1-dioxide (3).Treatment of 3 with piperidine produces the corresponding alkanethiol in situ quantitatively and subsequent treatment with various electrophiles gives the corresponding sulfides and thiocarboxylic S-esters in good yields.

EFFICIENT CONVERSION OF CARBOXYLIC ACIDS INTO THIOL ESTERS

A facile and direct preparation of thiol esters from carboxylic acids and thiols using diphenyl 2-oxo-3-oxazolinylphosphonate in the presence of triethylamine is described.

Preparation of 4--1,4-dihydropyridines and Their Use as Thiolate-transferring Agents

Alkane- (or arene)-thiols or thiolates add smoothly to esters or amides of 1-methylpyridinium-3,5-dicarboxylic acid salts; on treatment of these adducts with activated acid-derivatives, thioesters are formed in excellent yields.