5925-68-8Relevant academic research and scientific papers
Palladium Catalyzed Direct Carbonylative Thiomethylation of Aryldiazonium Salts and Amines with 4-(Methylthio)-2-Butanone as (Methylthio) Transfer Agent
Tian, Qingqiang,Xu, Shasha,Zhang, Chiying,Liu, Xinyi,Wu, Xiangwei,Li, Yahui
, p. 8797 - 8804 (2021/07/19)
Herein, an interesting palladium-catalyzed procedure for the direct carbonylative thiomethylation of aromatic amine derivatives with 4-methylthio-2-butanone is developed. Using 4-methylthio-2-butanone as (methylthio) transfer agent, a variety of corresponding thioesters are obtained with moderate to good yields under base-free condition. In addition, good functional group tolerance can be observed.
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.
Palladium-catalyzed intermolecular transthioetherification of aryl halides with thioethers and thioesters
Li, Yahui,Bao, Gao,Wu, Xiao-Feng
, p. 2187 - 2192 (2020/03/11)
Functional group transfer reactions are an important synthetic tool in modern organic synthesis. Herein, we developed a new palladium-catalyzed intermolecular transthioetherification reaction of aryl halides with thioethers and thioesters. The synthetic utility and practicality of this catalytic protocol are demonstrated in a wide range of successful transformations (>70 examples). This catalytic protocol is applicable in carbonylative coupling processes as well, and the first example of carbonylative methylthioesterification of aryl halides has been achieved. Notably, this work also provides an approach to using natural products, such as methionine and selenomethionine, as the functional group sources.
Electrophilic Activation of Carboxylic Anhydrides for Nucleophilic Acylation Reactions
Kumar, Varun,Kumar, Yashwant,Lal Meena, Chhuttan,Mahajan, Dinesh,Rana, Anil,Sharma, Nidhi
, p. 3902 - 3910 (2018/09/29)
Nucleophilic acylation of symmetrical carboxylic anhydrides has inherited limitation of reaction efficiency along with relatively poor reactivity. Traditionally, one equivalent carboxylic acid is generated during nucleophilic acylation of a symmetrical anhydride, which always limits the yield of final product to 50percent or less. This is a major drawback, which discourages the use of anhydrides for laboratory or industrial applications. Electrophilic activation of carboxylic anhydride using methanesulfonyl chloride is found to be an efficient method for nucleophilic acylation, which increases product yield by restricting the formation of corresponding acid as a side product. The developed protocol found to be a mild and high yielding methodology for one-pot nucleophilic acylation of carboxylic anhydrides with several type of N- and S-nucleophiles demonstrating appreciable functional group tolerance.
One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea
Abbasi, Mohammad,Khalifeh, Reza
supporting information, p. 1265 - 1273 (2015/08/18)
An efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3 N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thiourea with benzoic anhydrides, which were subjected to conjugate addition with electron-deficient alkenes or a nucleophilic displacement reaction with alkyl halides.
Synthesis of β-amino-α,β-unsaturated ketone derivatives via sequential rhodium-catalyzed sulfur ylide formation/rearrangement
He, Jun,Man, Zengming,Shi, Yinping,Li, Chuan-Ying
, p. 4816 - 4823 (2015/05/13)
In the presence of a Rh(II) catalyst and β-(methylthio)-α,β-unsaturated ketones, 1-sulfonyl-1,2,3-triazoles can be converted into functionalized β-amino-α,β-unsaturated ketones via formation of α-imino rhodium carbene/sulfur ylide and subsequent rearrangement. The products decompose to useful 2-methylthiopyrrole derivatives conveniently in high yield.
Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl- thiazolin-2-thione derivatives. Part III: An alkylthiol- and thioacid-free route to diversely substituted S-alkyl thioesters
Mehdid, Mohammed Amine,Djafri, Ayada,Andreoli, Federico,Vanthuyne, Nicolas,Farran, Daniel,Niebler, Johannes,Buettner, Andrea,Giorgi, Michel,Roussel, Christian
, p. 4994 - 5001 (2013/07/19)
A metal free synthesis of S-alkyl thioesters, which does not involve alkylthiol or thiocarboxylic acid as sulfur source is disclosed. The process involves first an acylation at the nitrogen of the readily available N-(2-aminophenyl)-4-methyl-thiazolin-2-thione, second an alkylation at sulfur of the resulting amides and finally a base catalyzed metathetic reaction, which provides under very mild conditions and in high isolated yields the S-alkyl thioesters. An ion-pair intermediate (9-acyl-3-methyl[1,3]thiazolo[3,2-a][3,1] benzimidazol-9-ium alkylthiolate) accounts for the formation of mixed thioesters during cross-coupling experiments. S-Alkyl diversity is provided by the alkylating agent and the acyl diversity comes from the acylating agent, while the sulfur atom is provided by the heterocycle.
Rhodium-catalyzed acyl-transfer reaction between benzyl ketones and thioesters: Synthesis of unsymmetric ketones by ketone CO-C bond cleavage and intermolecular rearrangement
Arisawa, Mieko,Kuwajima, Manabu,Toriyama, Fumihiko,Li, Guangzhe,Yamaguchi, Masahiko
supporting information; experimental part, p. 3804 - 3807 (2012/09/07)
In the presence of catalytic amounts of RhH(CO)(PPh3) 3 and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of keto
Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade
Thiel, Verena,Brinkhoff, Thorsten,Dickschat, Jeroen S.,Wickel, Susanne,Grunenberg, Joerg,Wagner-Doebler, Irene,Simon, Meinhard,Schulz, Stefan
experimental part, p. 234 - 246 (2010/04/29)
Bacteria of the Roseobacter clade are abundant marine bacteria and are important contributors to the global sulfur cycle. The volatiles produced by two of its members, Phaeobacter gallaeciensis and Oceanibulbus indolifex, were analyzed to investigate whether the released compounds are derived from sulfur metabolism, and which biosynthetic pathways are involved in their formation. Both bacteria emitted different sulfides and thioesters, including new natural compounds such as 5-methyl phenylethanethioate (16) and butyl methanesulfonate (21). The S-methyl alkanoates were identified by comparison with standards that were synthesized from the respective methyl alkanoates by a new method using an easily prepared aluminium/sulfur reagent. Phaeobacter gallaeciensis is also able to produce tropone (37) in large amounts. Its biosynthesis was investigated by various feeding experiments, showing that 37 is formed via a deviation of the phenylacetate catabolism. The unstable tropone hydrate 42 was identified as an intermediate of the tropone biosynthesis that was also released together with tropolone (38). The Royal Society of Chemistry 2010.
A Fast and Solvent-Free Conversion of Thioamides into Thioesters
Darabi, Hossein R.,Aghapoor, Kioumars,Tabar-Heidar, Kourosh
, p. 79 - 81 (2007/10/03)
Solvent-free irradiation of thiomorpholides with two kinds of methylating agents under microwave or ultrasonic conditions gave the corresponding thioesters in high yield. The method is simple and avoids prolonged heating with solvents.
