86763-31-7Relevant 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 (2018/05/31)
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.
One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea
Abbasi, Mohammad,Khalifeh, Reza
supporting information, p. 1265 - 1273 (2015/08/18)
An efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3 N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thiourea with benzoic anhydrides, which were subjected to conjugate addition with electron-deficient alkenes or a nucleophilic displacement reaction with alkyl halides.
Pd-catalyzed thiocarbonylation with stoichiometric carbon monoxide: Scope and applications
Burhardt, Mia N.,Taaning, Rolf H.,Skrydstrup, Troels
supporting information, p. 948 - 951 (2013/03/28)
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.
A Novel Synthesis of Thiocarboxylic S-Esters from 1-(Acylthio)ethaniminium Halides and Alkyl Halides Using Liquid-Liquid Phase-Transfer Catalysis
Takido, Toshio,Toriyama, Masaharu,Itabashi, Kunio
, p. 404 - 406 (2007/10/02)
S-Alkyl, S-benzyl, and S-(2-alkenyl) thiocarboxylates are prepared in good yields by acylation of thioacetamide with acyl halides and reaction of the resultant 1-(acylthio)ethaniminium halides with alkyl halides under liquid-liquid phase-transfer conditions.
