52532-97-5Relevant academic research and scientific papers
Microwave-assisted direct thioesterification of carboxylic acids
Chou, Yen-Lin,Jhong, Yi,Swain, Sharada Prasanna,Hou, Duen-Ren
, p. 10201 - 10208 (2017)
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.
Ligand exchange reaction of sulfoxides in organic synthesis: A versatile procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides
Satoh, Tsuyoshi,Unno, Hideaki,Mizu, Yasuhiro,Hayashi, Yasumasa
, p. 7843 - 7854 (2007/10/03)
A novel two-step procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides is described. Methylesters are reacted with lithium carbanion of chloromethyl phenyl sulfoxide to give α-chloro α-sulfinyl ketones in 70 to 90% yields. Potassium enolate of the α-chloro α-sulfinyl ketone was treated with tert-butyllithium at -78°C to give alkynolate via alkylidene carbenoid. This intermediate was treated with alcohols, thioles, 5% aqueous NaOH, and amine hydrochlorides to afford one-carbon homologated esters, thioesters, carboxylic acids and amides, respectively, in good to excellent yields.
