- Method for synthesizing thioester through cross-coupling of visible light-catalyzed sodium sulfinate and acyl chloride
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The method takes sodium sulfinate and acyl chloride as raw materials and utilizes 2, 6 - dimethyl -1, 4 - dihydro -3, 5 - pyridine dicarboxylic acid diethyl ester and an organic alkali catalytic system to cross-couple sulfur radicals and acyl radicals und
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Paragraph 0040-0043
(2021/09/11)
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- Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds
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The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.
- Xu, Kaiqiang,Liu, Long,Li, Zhaohui,Huang, Tianzeng,Xiang, Kang,Chen, Tieqiao
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p. 14653 - 14663
(2020/12/29)
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- Na2CO3-promoted thioesterification via N–C bond cleavage of amides to construct thioester derivatives
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A mild, efficient, and transition-metal-free catalytic strategy is developed to construct thioesters via selective N–C bond cleavage of Boc2-activated primary amides. This strategy is successfully carried out with stoichiometric Na2C
- Tao, Jiasi,Yu, Weijie,Luo, Jin,Wang, Tao,Ge, Wanling,Zhang, Ziwei,Yang, Bingjie,Xiong, Fei
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p. 486 - 492
(2019/11/03)
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- Oxalic Acid Monothioester for Palladium-Catalyzed Decarboxylative Thiocarbonylation and Hydrothiocarbonylation
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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.
- Zhao, Bin,Fu, Yao,Shang, Rui
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p. 9521 - 9526
(2019/11/28)
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- Method for producing thioesters by means of oxo thio acetic acid compounds
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The invention provides a method for preparing thioesters from oxo thio acetic acid compounds. In the presence of a palladium catalyst, a phosphine ligand and an organic solvent, an oxo thio acetic acid compound is decarboxylated and then reacts with an ar
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Paragraph 0056; 0057; 0242; 0248
(2019/12/02)
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- Metal-free thioesterification of amides generating acyl thioesters
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A base-initiated thioesterification of amides with various thiols is reported. This reaction can take place efficiently under metal-free and air-atmospheric conditions, and provides a facile and practically useful approach to the synthesis of valuable acy
- Wang, Qun,Liu, Long,Dong, Jianyu,Tian, Zhibin,Chen, Tieqiao
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supporting information
p. 9384 - 9388
(2019/06/21)
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- Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters
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A convenient visible-light photoredox catalysis has been developed for the synthesis of thioesters from two readily available starting materials: acid chlorides and sodium sulfinates. The facile generation of acyl radical species under the visible light photoredox conditions allows the formation of thiyl radical species from sodium sulfinates via multiple single electron transfer reactions, where the final acyl radical-thiyl radical coupling has been accomplished. The direct radical-radical coupling strategy offers a mild and controlled photochemical approach to important synthetic building blocks such as thioesters.
- Bogonda, Ganganna,Patil, DIlip V.,Kim, Hun Young,Oh, Kyungsoo
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supporting information
p. 3774 - 3779
(2019/05/24)
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- Catalyst-free direct decarboxylative coupling of α-keto acids with thiols: a facile access to thioesters
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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.
- Yan, Kelu,Yang, Daoshan,Wei, Wei,Zhao, Jing,Shuai, Yuanyuan,Tian, Laijin,Wang, Hua
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p. 7323 - 7330
(2015/07/01)
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- Metal-free sp3 C-H functionalization: A novel approach for the syntheses of selenide ethers and thioesters from methyl arenes
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A DTBP-promoted metal-free and solvent-free formation of C-Se and C-S bonds through sp3 C-H functionalization of methyl arenes with diselenides and disulfides is described. the Partner Organisations 2014.
- Badsara, Satpal Singh,Liu, Yi-Chen,Hsieh, Ping-An,Zeng, Jing-Wen,Lu, Shao-Yi,Liu, Yi-Wei,Lee, Chin-Fa
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supporting information
p. 11374 - 11377
(2014/11/08)
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- Synthesis of thiol esters using nano CuO/Ionic liquid as an eco-friendly reductive system under microwave irradiation
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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
- Azeredo, Juliano B.,Godoi, Marcelo,Schwab, Ricardo S.,Botteselle, Giancarlo V.,Braga, Antonio L.
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supporting information
p. 5188 - 5194
(2013/11/06)
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- Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors
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A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh 3)4-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6- tetrafluorobenzenes.
- Arisawa, Mieko,Yamada, Toru,Yamaguchi, Masahiko
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supporting information; experimental part
p. 6090 - 6092
(2011/01/04)
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- Photochemistry of Bis(sulfonyl)diazomethanes
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The photochemistry of a series of bis(sulfonyl)diazomethanes was investigated in solution and in low temperature matrices. These diazo compounds are of interest as photoacid generators in photoresists for deep UV lithography. Triplet carbenes could be trapped in solution, but attempts to isolate the carbenes in argon matrices at 10 K were unsuccessful, the corresponding sulfenes and other rearranged products being observed under these conditions instead. This is in line with DFT and ab initio calculations, which predict the singlet carbenes to be transition states on the pathway to oxathiirene oxides, which can be looked upon as intramolecularly stabilized carbenes. The triplet carbenes lie energetically above the singlet transition states and so are not expected to have a prolonged lifetime even in low-temperature matrices.
- Sander, Wolfram,Strehl, Anja,Winkler, Michael
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p. 3771 - 3778
(2007/10/03)
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- Cobalt carbonyl catalyzed reaction of mercaptans with Schiff bases and carbon monoxide
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Thiophenols and p-methylbenzyl mercaptan react with Schiff bases and carbon monoxide in benzene, in the presence of cobalt carbonyl, to give amides as the pricipal products.These amides arise from cleavage of the carbon-nitrogen double bond of the reactant imine.The reaction is applicable to a variety of Schiff bases (i.e. aliphatic, benzylic, aromatic).Thioesters and olefins are usually obtained as reaction by-products.
- Antebi, Shlomo,Alper, Howard
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p. 2010 - 2012
(2007/10/02)
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- COBALT CARBONYL CATALYZED REACTIONS OF DISULFIDES: CARBONYLATION TO THIOESTERS AND DESULFURIZATION TO SULFIDES.
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Aromatic and benzylic disulfides react with carbon monoxide and a catalytic amount of cobalt carbonyl to give thioesters and carbonyl sulfide, while the presence of t-butyl peroxide results in the formation of sulfides in high yields.
- Antebi, Shlomo,Alper, Howard
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p. 2609 - 2612
(2007/10/02)
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