3128-42-5Relevant academic research and scientific papers
Zeolite Beta nanoparticles assembled Cu catalysts with superior catalytic performances in the synthesis of thioesters by cross-coupling of aldehydes and disulfides
Zheng, Xiang,Fu, Wenqian,Xiong, Jing,Xi, Jiachen,Ni, Xiaojun,Tang, Tiandi
, p. 152 - 157 (2016)
Development of the highly active and stable heterogeneous transition metal catalysts is of great importance in synthetic chemistry. Herein, zeolite Beta nanoparticles assembled Cu catalyst (Cu-Beta-Nano) with high external surface area was directly synthe
Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
Yano De Albuquerque, Danilo,Teixeira, Wystan K. O.,Sacramento, Manoela Do,Alves, Diego,Santi, Claudio,Schwab, Ricardo S.
supporting information, p. 595 - 605 (2022/01/12)
A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.
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
Synthesis of selenol esters via the reaction of acyl chlorides with diselenides in the presence of Zn dust catalyzed by CoCl2·6H2O
Dall'Oglio, Evandro L.,Stein, André L.,Vasconcelos, Leonardo G.,Vieira, Lucas C. C.,de Oliveira, Angélica J.,de Oliveira, Sandynara A.
supporting information, (2021/08/25)
A practical and efficient approach for the synthesis of selenol and thiol esters is described via the reaction of acyl chlorides with diselenides or disulfides in the presence of Zn dust catalyzed by inexpensive CoCl2·6H2O This proto
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.
Method for preparing benzoic acid-S-phenyl ester compound through cuprous catalysis
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Paragraph 0043-0046, (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.
Thioesterification and Selenoesterification of Amides via Selective N-C Cleavage at Room Temperature: N-C(O) to S/Se-C(O) Interconversion
Li, Guangchen,Rahman, Md. Mahbubur,Szostak, Michal
supporting information, p. 1060 - 1066 (2020/04/01)
The direct nucleophilic addition to amides represents an attractive methodology in organic synthesis that tackles amidic resonance by ground-state destabilization. This approach has been recently accomplished with carbon, nitrogen and oxygen nucleophiles.
Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light
Zhang, Yueteng,Ji, Peng,Hu, Wenbo,Wei, Yongyi,Huang, He,Wang, Wei
supporting information, p. 8225 - 8228 (2019/07/16)
A metal- and oxidant-free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10-phenanthrenequinone-promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late-stage modification of complex structures, which are difficult to achieve with the existing protocols.
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.
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.
