60718-19-6Relevant academic research and scientific papers
Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
supporting information, p. 8098 - 8103 (2021/10/25)
We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.
Manganese(iii)-promoted thiocarbonylation of alkylborates with disulfides: synthesis of aliphatic thioesters
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 9654 - 9658 (2021/12/01)
A Mn(iii)-promoted thiocarbonylation procedure toward the synthesis of thioesters has been developed. By employing easily available disulfides and potassium alkyltrifluoroborates as the starting materials, and cheap and non-toxic Mn(OAc)3·2H2O as the promotor, a broad range of thioesters were synthesized in good to excellent yieldsviaradical intermediates.
Synthesis of thiol esters using nano CuO/Ionic liquid as an eco-friendly reductive system under microwave irradiation
Azeredo, Juliano B.,Godoi, Marcelo,Schwab, Ricardo S.,Botteselle, Giancarlo V.,Braga, Antonio L.
supporting information, p. 5188 - 5194 (2013/11/06)
We report an efficient, fast, and environmentally friendly method for the synthesis of a wide range of thiol esters using stable diorganoyl disulfides and acyl chlorides, using CuO nanoparticles and [pmim]Br as the reductive system. This method gave good to excellent isolated yields of the desired products after only three minutes of microwave irradiation. Furthermore, by using the same green approach, we were also able to synthesize thiocarbonates bearing interesting functionalities. We report an efficient, fast, and environmentally friendly method for the synthesis of thiol esters starting from diorganoyl disulfides and acyl chlorides, and using CuO nanoparticles and [pmim]Br as the reductive system. This approach gave good to excellent isolated yields of the desired products in only three minutes under microwave irradiation. Copyright
S-Acylation of aliphatic and aromatic thiols with carboxylic acids and their esters over solid acid catalysts in the gas phase at temperatures above 200 °c
Nagashima, Sayoko,Yamazaki, Hitomi,Kudo, Kentaro,Kamiguchi, Satoshi,Chihara, Teiji
, p. 332 - 338 (2013/07/26)
Benzenethiol is reacted with acetic acid in a hydrogen stream over [(Mo6Cl8)Cl4(H2O) 2]·6H2O. Catalytic activity of the clusters appears above 200 °C, yielding S-phenyl thioacetate. The selectivity is 98% at 300 °C. Niobium, tantalum, and tungsten halide clusters with the same octahedral metal framework also catalyze the reaction. Benzoic acid and aliphatic carboxylic acids afford the corresponding S-phenyl carbothioates by reaction with benzenethiol. Aliphatic thiols are also S-acylated to yield the corresponding S-alkyl carbothioates. When carboxylic esters are applied to the reaction with benzenethiol over [(Nb6Cl12)Cl 2(H2O)4]·4H2O at 450 °C, the sterically unhindered moiety of the ester is incorporated into the products: S-phenyl thioacetate or methyl phenyl sulfide is obtained selectively. A Br?nsted acid site developed on the cluster complex by thermal activation is the active site of the catalyst. Hence, solid acids such as silica-alumina, zeolites, and heteropoly acids that are stable above 200 °C also catalyze these reactions.
Synthesis of thiol esters by the reaction of ricinoleic acid with thiols under solvent-free conditions
Lara, Renata G.,Rodrigues, Dielson C.,Mendes, Samuel R.,Panatieri, Rodrigo B.,Jacob, Raquel G.,Alves, Diego,Lenardao, Eder J.,Perin, Gelson
experimental part, p. 2974 - 2984 (2011/09/12)
The synthesis of several ricinoleic acid thiol esters starting from cis-(R)-12-hydroxyoctadec-9-enoic acid and thiols in the presence of N,N'-dicyclohexylcarbodiimide (DCC) is described. The method is efficient for aromatic and aliphatic thiols, selective
Ionic liquid: An efficient and reusable media for seleno- and thioester synthesis promoted by indium
Tabarelli, Greice,Alberto, Eduardo E.,Deobald, Anna M.,Marin, Graciane,Rodrigues, Oscar E.D.,Dornelles, Luciano,Braga, Antonio L.
experimental part, p. 5728 - 5731 (2010/11/16)
A series of thio and selenoesters were efficiently obtained employing stable diorganyl chalcogenides, acyl chlorides, and In as reducing agent in BMIM·PF6. Recycling of the ionic liquid was also performed, which was reused three times.
Rapid and convenient thioester synthesis under phase-transfer catalysis conditions
Simion, Cristian,Hashimoto, Iwao,Mitoma, Yoshiharu,Simion, Alina Marieta,Egashira, Naoyoshi
experimental part, p. 2480 - 2488 (2011/02/23)
Various thioesters were obtained through an efficient phase-transfer catalysis method, by treating several thiophenols with different acyl chlorides, in a biphasic system composed of 10% aqueous NaOH and dichloromethane in the presence of tetrabutylammonium chloride. The thiolation reaction was complete in only 5 minutes, at 0C. Taylor & Francis Group, LLC.
Convenient and efficient synthesis of thiol esters using zinc oxide as a heterogeneous and eco-friendly catalyst
Bandgar, Babasaheb Pandurang,More, Parmeshwar Eknath,Kamble, Vinod Tribhuvannathji,Sawant, Sanjay Suresh
experimental part, p. 1006 - 1010 (2009/04/05)
A catalytic method was developed to synthesize thiol esters from the reaction of acyl chlorides and thiols using zinc oxide as a catalyst under solvent-free conditions at room temperature. Mild reaction conditions, short reaction time, excellent yields of products and recyclability of the catalyst are noteworthy features of this methodology. CSIRO 2008.
Zinc promoted convenient and general synthesis of thiol esters
Meshram,Reddy, Gondi Sudershan,Bindu, K. Hima,Yadav
, p. 877 - 878 (2007/10/03)
Synthesis of thiol esters from acyl chlorides and thiols in the presence of activated zinc is described. The recovery of zinc and its reuse makes the procedure more economic.
