90172-73-9Relevant 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
Visible-Light-Mediated Cross Dehydrogenative Coupling of Thiols with Aldehydes: Metal-Free Synthesis of Thioesters at Room Temperature
Roy, Vishal Jyoti,Sen, Partha Pratim,Raha Roy, Sudipta
, p. 16965 - 16976 (2021/11/18)
Thioesters play a crucial role in biological systems and serve as important building blocks for organic synthesis. Herein, Eosin Y and TBHP mediated photochemical cross dehydrogenative coupling (PCDC) between feedstock aldehydes and thiols has been descri
Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
, p. 10829 - 10837 (2021/07/28)
Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.
Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
supporting information, p. 8098 - 8103 (2021/10/25)
We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.
Method for preparing benzoic acid-S-phenyl ester compound through cuprous catalysis
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Paragraph 0059-0062, (2020/12/09)
The invention discloses a method for preparing a benzoic acid-S-phenyl ester compound shown as a formula (IV) through cuprous catalysis. The preparation method comprises the following steps of: preparing a reaction product from a benzaldehyde compound shown as a formula (I), elemental sulfur shown as a formula (II) and an iodobenzene compound shown as a formula (III) by using cuprous iodide as a catalyst, tetraethylammonium bromide as an alkali and N, N-dimethylformamide as a medium, and carrying out post-treatment on the reaction product to obtain the benzoic acid-S-phenyl ester compound, wherein the formulas are described in the specification. The method is efficient in chemical agent and low in cost; and the catalytic system has wide adaptability and is suitable for large-scale production of chemical intermediates.
Trithioorthoester Exchange and Metathesis: New Tools for Dynamic Covalent Chemistry
Bothe, Michael,Furlan, Ricardo L. E.,Orrillo, A. Gastón,Von Delius, Max
supporting information, p. 1988 - 1994 (2019/10/22)
To expand the toolbox of dynamic covalent and systems chemistry, we investigated the acid-catalyzed exchange reaction of trithioorthoesters with thiols. We found that trithioorthoester exchange occurs readily in various solvents in the presence of stoichiometric amounts of strong Bronsted acids or catalytic amounts of certain Lewis acids. The scope of the exchange reaction was explored with various substrates, and conditions were identified that permit clean metathesis reactions between two different trithioorthoesters. One distinct advantage of S, S, S-orthoester exchange over O, O, O-orthoester exchange is that the exchange reaction can kinetically outcompete hydrolysis, thereby making the process less sensitive to residual moisture. We expect that the relatively high stability of the products might be beneficial in future supramolecular receptors or porous materials.
Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts
Liu, Chengwei,Szostak, Michal
supporting information, p. 2130 - 2133 (2018/03/06)
A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest.
Highly Active Manganese-Mediated Acylation of Alcohols with Acid Chlorides or Anhydrides
Joo, Seong-Ryu,Youn, Young-Jin,Hwang, Young-Ran,Kim, Seung-Hoi
, p. 2665 - 2669 (2017/10/07)
To explore further the practical uses of highly active manganese (Mn?), a variety of alcohols were treated with Mn?, and the resulting complexes were coupled with acid chlorides and/or acetic anhydride in the absence of any extra catalyst. The subsequent reactions took place smoothly under mild conditions, providing the corresponding O-acylation products in good to excellent isolated yields.
A synthesis of biaryl ketones via the C–S bond cleavage of thiol ester by a Cu/Ag salt
Ghosh, Prasanjit,Ganguly, Bhaskar,Das, Sajal,Perl, Eliyahu
supporting information, p. 2751 - 2756 (2017/06/23)
We report the synthesis of biaryl ketones via an unprecedented copper/silver catalyzed acylative cross-coupling of thiol esters with either an arylboronic acid or a potassium aryltrifluoroborate. This new method proceeds without a requisite Pd-catalyst and Cu(I)TC mediator, and is efficient, versatile, operationally simple, and accommodating functionally diverse thiol esters, arylboronic acids, and potassium aryltrifluoroborates.
Formation of C(sp2)-S bonds through decarboxylation of α-oxocarboxylic acids with disulfides or thiophenols
Rong, Guangwei,Mao, Jincheng,Liu, Defu,Yan, Hong,Zheng, Yang,Chen, Jie
, p. 26461 - 26464 (2015/03/30)
Copper-catalyzed decarboxylative coupling between α-oxocarboxylic acids and diphenyl disulfides or thiophenols is presented, which provided an effective and direct approach for the preparation of useful thioesters through C(sp2)-S bond formatio
