77750-06-2Relevant academic research and scientific papers
Method for synthesizing thioester through cross-coupling of visible light-catalyzed sodium sulfinate and acyl chloride
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Paragraph 0052-0055, (2021/09/11)
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
Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds
Xu, Kaiqiang,Liu, Long,Li, Zhaohui,Huang, Tianzeng,Xiang, Kang,Chen, Tieqiao
, p. 14653 - 14663 (2020/12/29)
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.
Nickel-Catalyzed Thiocarbonylation of Arylboronic Acids with Sulfonyl Chlorides for the Synthesis of Thioesters
Qi, Xinxin,Bao, Zhi-Peng,Yao, Xin-Tong,Wu, Xiao-Feng
supporting information, p. 6671 - 6676 (2020/09/02)
An interesting procedure for thioester synthesis via nickel-catalyzed thiocarbonylation of arylboronic acid with sulfonyl chlorides as the sulfur source has been explored. Using Mo(CO)6 as a solid CO surrogate and reductant, a broad range of thioesters were obtained in moderate to good yields with good functional group tolerance.
Oxalic Acid Monothioester for Palladium-Catalyzed Decarboxylative Thiocarbonylation and Hydrothiocarbonylation
Zhao, Bin,Fu, Yao,Shang, Rui
, 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.
Na2CO3-promoted thioesterification via N–C bond cleavage of amides to construct thioester derivatives
Tao, Jiasi,Yu, Weijie,Luo, Jin,Wang, Tao,Ge, Wanling,Zhang, Ziwei,Yang, Bingjie,Xiong, Fei
, p. 486 - 492 (2019/11/03)
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
Air-Tolerant Direct Thiol Esterification with Carboxylic Acids Using Hydrosilane via Simple Inorganic Base Catalysis
Xuan, Maojie,Lu, Chunlei,Liu, Meina,Lin, Bo-Lin
, p. 7694 - 7701 (2019/06/27)
Direct thioesterification of carboxylic acids with thiols using nontoxic activation agents is highly desirable. Herein, an efficient and practical protocol using safe and inexpensive industrial waste polymethylhydrosiloxane as the activation agent and K3PO4 with 18-crown-6 as a catalyst is described. Various functional groups on carboxylic acid and thiol substituents can be tolerated by the present system to afford thioesters in yields of 19-100%.
Metal-free thioesterification of amides generating acyl thioesters
Wang, Qun,Liu, Long,Dong, Jianyu,Tian, Zhibin,Chen, Tieqiao
supporting information, p. 9384 - 9388 (2019/06/21)
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
Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters
Bogonda, Ganganna,Patil, DIlip V.,Kim, Hun Young,Oh, Kyungsoo
supporting information, p. 3774 - 3779 (2019/05/24)
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.
Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors
Arisawa, Mieko,Yamada, Toru,Yamaguchi, Masahiko
supporting information; experimental part, p. 6090 - 6092 (2011/01/04)
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.
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.
