39248-93-6Relevant academic research and scientific papers
Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
Yano De Albuquerque, Danilo,Teixeira, Wystan K. O.,Sacramento, Manoela Do,Alves, Diego,Santi, Claudio,Schwab, Ricardo S.
supporting information, p. 595 - 605 (2022/01/12)
A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.
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
Oxalic Acid Monothioester for Palladium-Catalyzed Decarboxylative Thiocarbonylation and Hydrothiocarbonylation
Zhao, Bin,Fu, Yao,Shang, Rui
supporting information, p. 9521 - 9526 (2019/11/28)
Oxalic acid monothioester (OAM), an easily accessible and storable reagent, was reported herein as a thioester synthetic equivalent for palladium-catalyzed decarboxylative thiocarbonylation of organohalides and hydrothiocarbonylation of unsaturated carbon-carbon bonds at room temperature with high chemo- and regioselectivity. The reaction is applicable to the synthesis of cysteine-derived thioesters, thus allowing chemical modification of cysteine-containing peptides. Decarboxylation of OAM proceeds through oxidative addition of Pd(0) to the acyl-S bond, which accounts for the very mild reaction conditions.
Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light
Zhang, Yueteng,Ji, Peng,Hu, Wenbo,Wei, Yongyi,Huang, He,Wang, Wei
supporting information, p. 8225 - 8228 (2019/07/16)
A metal- and oxidant-free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10-phenanthrenequinone-promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late-stage modification of complex structures, which are difficult to achieve with the existing protocols.
Catalyst-free direct decarboxylative coupling of α-keto acids with thiols: a facile access to thioesters
Yan, Kelu,Yang, Daoshan,Wei, Wei,Zhao, Jing,Shuai, Yuanyuan,Tian, Laijin,Wang, Hua
, p. 7323 - 7330 (2015/07/01)
A novel, efficient, and catalyst-free strategy has been initially developed for the construction of thioesters via the direct radical oxidative decarboxylation of α-keto acids with thiols, and the corresponding target products were obtained in moderate to good yields. It offers an alternative approach for the synthesis of useful diverse thioesters.
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
Metal-free cross-coupling reaction of aldehydes with disulfides by using DTBP as an oxidant under solvent-free conditions
Zeng, Jing-Wen,Liu, Yi-Chen,Hsieh, Ping-An,Huang, Yu-Ting,Yi, Chih-Lun,Badsara, Satpal Singh,Lee, Chin-Fa
, p. 2644 - 2652 (2014/05/06)
A DTBP-promoted C-H thiolation of aldehydes with disulfides under metal-free and solvent-free conditions is described. The system shows good functional group tolerance to afford thioesters in moderate to excellent yields. the Partner Organisations 2014.
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
Palladium-catalyzed coupling of thiol esters with aryl and primary and secondary alkyl organoindium reagents
Fausett, Bryan W.,Liebeskind, Lanny S.
, p. 4851 - 4853 (2007/10/03)
Thiol esters and organoindium reagents undergo palladium-catalyzed cross-coupling under mild conditions to give ketones in moderate to excellent yields. Aryl and primary/ secondary alkyl organoindium reagents can be used as coupling partners. This method has two advantages over the cross-coupling of thiol esters with boron and tin reagents: (1) no added copper reagent is required to mediate the reaction and (2) for the case of alkyl transfer, no added base is required to activate organoindium reagents for cross-coupling as is required for the coupling of alkyl boron reagents with thiol esters.
