6631-86-3Relevant academic research and scientific papers
Methanesulfonic anhydride-promoted sustainable synthesis of thioesters from feedstock acids and thiols
Singh, Pallavi,Peddinti, Rama Krishna
, (2021/02/22)
Abstract: An unprecedented metal-, halogen- and solvent-free, MSAA-promoted S-carbonylation of thiols with feedstock acids has been developed. This new transformation provides an efficient and atom-economic strategy for the synthesis of thioesters in a single operation from readily available and inexpensive starting materials. The reaction avoids the use of expensive and hazardous coupling reagents, bases and generates water as the only by-product, thus making this chemical synthetic process more viable, environment-friendly and contributing towards sustainable chemistry. Graphic abstract: [Figure not available: see fulltext.].
Green synthesis and antibacterial activity of chalcogenoesters
Baldisserotto, Bernardo,Dornelles, Luciano,Junior, Guerino B.,Ravanello, Bruno B.,Rodrigues, Oscar E. D.,Santos, Roberto C. V.,Soares, Letiére C.,da Rosa, Fernanda H.,da Silva, Rafael S.,de A. Vaucher, Rodrigo,dos S. Barboza, Victor
, (2020/03/31)
Abstract: Herein, we present a new variation for an eco-friendly methodology for the synthesis of chalcogenoester in good-to-excellent yields in a short time, with an easy work-up/purification step, and in a greenest methodology, affording the minimum gen
Harnessing the catalytic behaviour of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP): An expeditious synthesis of thioesters
Singh, Pallavi,Peddinti, Rama Krishna
supporting information, p. 1875 - 1878 (2017/04/21)
A novel, efficient, metal-, base- and acid-free straightforward protocol has been developed for the construction of useful thioesters. The immense catalytic potential of HFIP for promoting the thiocarbonylation of acyl halides and thiols is disclosed. HFIP was recovered with ease and reused for further reactions without any loss of reactivity. Both aryl and alkyl thiols bearing electron-donating and electron-withdrawing groups as well as aryl- and alkyl acyl halides worked well in this reaction. Inexpensive precursors, short reaction time, obviating workup, high atom economy, and gram-scale preparation are the significant features of the developed eco-friendly route for S-carbonylation of thiols.
Direct oxidative coupling of thiols and benzylic ethers via C(sp3)-H activation and C-O cleavage to lead thioesters
Feng,Lv,Lu,Cai
supporting information, p. 677 - 681 (2015/02/19)
An unprecedented C-S formation method via direct oxidative C(sp3)-H bond functionalization and C-O cleavage of benzylic ethers was developed. Various thioesters including thioester structure containing drug intermediates could be achieved by th
Iron-catalyzed thioesterification of methylarenes with thiols in water
Wang, Liang,Cao, Jing,Chen, Qun,He, Ming-Yang
supporting information, p. 7190 - 7193 (2015/01/16)
An iron-catalyzed coupling reaction of methylarenes with thiols leading to thioesters has been developed. The reactions were carried out in water with tert-butyl hydroperoxide (TBHP) as the oxidant and polyoxyethanyl α-tocopheryl sebacate (PTS) as the sur
Selective approach to thioesters and thioethers via sp3 C-H activation of methylarenes
Feng,Lu,Cai
, p. 54409 - 54415 (2015/01/16)
Novel C-S cross-dehydrogenative coupling (CDC) approaches for the selective synthesis of thioesters and thioethers have been developed via sp3 C-H activation of methylarenes and subsequent functionalization. The reaction of methylarenes with thiols resulted in thioesters in the presence of a FeBr2/TBHP system, while treatment of methylarenes with thiols in the Pd(OAc)2/O2/TBHP system led to the formation of thioethers. Both the green protocols demonstrate good functional group tolerance and satisfactory yields. This journal is
The direct thioesterification of aldehydes with disulfides via NHC-catalyzed carbonyl umpolung strategy
Singh, Santosh,Yadav, Lal Dhar S.
experimental part, p. 5136 - 5140 (2012/09/22)
An efficient N-heterocyclic carbene (NHC)-catalyzed direct thioesterification of aldehydes and α,β-unsaturated aldehydes (enals) with diaryl disulfides is reported. The protocol involves carbonyl umpolung reactivity of aldehydes and enals in which the car
Kinetics and Mechanism of the Aminolysis of S-Phenyl Thiobenzoates
Lee, Ikchoon,Shim, Chang Sub,Lee, Hai Whang
, p. 769 - 793 (2007/10/02)
Kinetic studies on the nucleophilic substitution reaction of S-phenyl thiobenzoates with anilines have been carried out at 55.0 deg C.Effects of substituents in the nucleophile(X), substrate(Y) and leaving groups(Z) are analyzed in terms of Hammett's and Broensted's coefficients, ρi and βi and cross-interaction constants ρij and βij where i and j denote X, Y or Z.The sign of ρXZ (or βXZ) is positive, and accordingly, the transition state(TS) variations with the substituents are consistent with those predicted by the potential energy surface diagram; the magnitude of ρx(βx) and ρxy decreases with a better leaving group, and that of ρz and βz decreases with a stronger nucleophile leading to an earlier TS, in agreement with a normal Hammond effect.The larger magnitudes of ρXY, ρYZ and βXZ suggest that the reaction proceeds by an associative SN2 mechanism.A greater kH/kD value (1.0) is observed with deuterated aniline nucleophiles for a stronger nucleophile and a better leaving group, supporting the earlier TS proposed on the basis of the cross-interaction constants.The inverse secondary kinetic isotope effects obtained preclude involvement of any four-center TS or base catalysis by aniline.
