53271-44-6Relevant academic research and scientific papers
Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides
Xie, Shimin,Su, Lebin,Mo, Min,Zhou, Wang,Zhou, Yongbo,Dong, Jianyu
, p. 739 - 749 (2021/01/09)
An alternative thioesterification reaction via copper-catalyzed oxidative coupling of readily available aroylhydrazides with disulfides is developed, in which oxidative expulsion of N2 overcomes the activation barrier between the carboxylic acid derivativ
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.].
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.
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.
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
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.
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
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%.
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.
Synthesis of 2-Aminoazoles from Thioesters via α-Heterosubstituted Ketones by Copper-Mediated Cross-Coupling
Kobayashi, Hiroyuki,Eickhoff, John A.,Zakarian, Armen
, p. 9989 - 9999 (2015/11/03)
Facile synthesis of a variety of α-heterosubstituted ketones under mild conditions was achieved by copper-mediated cross-coupling of thioesters with functionalized organostannanes. Application of this coupling methodology provided a concise pathway for the conversion of carboxylic acids to 2-aminoimidazoles, 2-aminothiazoles, and 2-aminooxazoles via thioesters in practical yields.
