- Zeolite Beta nanoparticles assembled Cu catalysts with superior catalytic performances in the synthesis of thioesters by cross-coupling of aldehydes and disulfides
-
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
- Zheng, Xiang,Fu, Wenqian,Xiong, Jing,Xi, Jiachen,Ni, Xiaojun,Tang, Tiandi
-
-
Read Online
- Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
-
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.
- 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)
-
- Synthesis of selenol esters via the reaction of acyl chlorides with diselenides in the presence of Zn dust catalyzed by CoCl2·6H2O
-
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
- 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)
-
- Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
-
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.
- Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
-
p. 10829 - 10837
(2021/07/28)
-
- Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides
-
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
- Xie, Shimin,Su, Lebin,Mo, Min,Zhou, Wang,Zhou, Yongbo,Dong, Jianyu
-
p. 739 - 749
(2021/01/09)
-
- Method for preparing benzoic acid-S-phenyl ester compound through cuprous catalysis
-
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.
- -
-
Paragraph 0043-0046
(2020/12/09)
-
- Thioesterification and Selenoesterification of Amides via Selective N-C Cleavage at Room Temperature: N-C(O) to S/Se-C(O) Interconversion
-
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.
- Li, Guangchen,Rahman, Md. Mahbubur,Szostak, Michal
-
supporting information
p. 1060 - 1066
(2020/04/01)
-
- Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light
-
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.
- Zhang, Yueteng,Ji, Peng,Hu, Wenbo,Wei, Yongyi,Huang, He,Wang, Wei
-
supporting information
p. 8225 - 8228
(2019/07/16)
-
- Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts
-
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.
- Liu, Chengwei,Szostak, Michal
-
supporting information
p. 2130 - 2133
(2018/03/06)
-
- A synthesis of biaryl ketones via the C–S bond cleavage of thiol ester by a Cu/Ag salt
-
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.
- Ghosh, Prasanjit,Ganguly, Bhaskar,Das, Sajal,Perl, Eliyahu
-
supporting information
p. 2751 - 2756
(2017/06/23)
-
- Catalyst-free direct decarboxylative coupling of α-keto acids with thiols: a facile access to thioesters
-
A novel, efficient, and catalyst-free strategy has been initially developed for the construction of thioesters via the direct radical oxidative decarboxylation of α-keto acids with thiols, and the corresponding target products were obtained in moderate to good yields. It offers an alternative approach for the synthesis of useful diverse thioesters.
- Yan, Kelu,Yang, Daoshan,Wei, Wei,Zhao, Jing,Shuai, Yuanyuan,Tian, Laijin,Wang, Hua
-
p. 7323 - 7330
(2015/07/01)
-
- Formation of C(sp2)-S bonds through decarboxylation of α-oxocarboxylic acids with disulfides or thiophenols
-
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
- Rong, Guangwei,Mao, Jincheng,Liu, Defu,Yan, Hong,Zheng, Yang,Chen, Jie
-
p. 26461 - 26464
(2015/03/30)
-
- Metal-free sp3 C-H functionalization: A novel approach for the syntheses of selenide ethers and thioesters from methyl arenes
-
A DTBP-promoted metal-free and solvent-free formation of C-Se and C-S bonds through sp3 C-H functionalization of methyl arenes with diselenides and disulfides is described. the Partner Organisations 2014.
- Badsara, Satpal Singh,Liu, Yi-Chen,Hsieh, Ping-An,Zeng, Jing-Wen,Lu, Shao-Yi,Liu, Yi-Wei,Lee, Chin-Fa
-
supporting information
p. 11374 - 11377
(2014/11/08)
-
- Polymer supported Pd catalyzed thioester synthesis via carbonylation of aryl halides under phosphine free conditions
-
A new polymer supported phosphine free Pd(ii) complex has been synthesized and characterized. The catalytic performance of the complex has been tested for the carbonylation of aryl halides into aryl thioesters under mild reaction conditions. Thioesters were obtained in excellent yields from various aryl iodides and thiols in the presence of carbon monoxide and polymer supported palladium catalyst. The effects of solvent, base, reaction time and catalyst amount for the thioester synthesis were reported. This catalyst showed excellent catalytic activity and recyclability. The polymer supported Pd(ii) catalyst could be easily recovered by filtration and reused more than five times without appreciable loss of its initial activity.
- Islam, Sk Manirul,Molla, Rostam Ali,Roy, Anupam Singha,Ghosh, Kajari
-
p. 26181 - 26192
(2014/07/08)
-
- Metal-free cross-coupling reaction of aldehydes with disulfides by using DTBP as an oxidant under solvent-free conditions
-
A DTBP-promoted C-H thiolation of aldehydes with disulfides under metal-free and solvent-free conditions is described. The system shows good functional group tolerance to afford thioesters in moderate to excellent yields. the Partner Organisations 2014.
- Zeng, Jing-Wen,Liu, Yi-Chen,Hsieh, Ping-An,Huang, Yu-Ting,Yi, Chih-Lun,Badsara, Satpal Singh,Lee, Chin-Fa
-
p. 2644 - 2652
(2014/05/06)
-
- Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions
-
Thiol and selenol esters were synthesized by a direct oxidative coupling reaction of aldehydes with disulfides or diselenides in ethyl acetate under metal-free conditions. Among the oxidants examined, tert-butyl peroxide (TBP) was shown to give the best results. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderate to good yields. Compared with the previous method, the present route is very simple, atom-economical and environmentally friendly. This journal is the Partner Organisations 2014.
- He, Chunhuan,Qian, Xuewei,Sun, Peipei
-
supporting information
p. 6072 - 6075
(2014/08/05)
-
- Synthesis of thiol esters using nano CuO/Ionic liquid as an eco-friendly reductive system under microwave irradiation
-
We report an efficient, fast, and environmentally friendly method for the synthesis of a wide range of thiol esters using stable diorganoyl disulfides and acyl chlorides, using CuO nanoparticles and [pmim]Br as the reductive system. This method gave good to excellent isolated yields of the desired products after only three minutes of microwave irradiation. Furthermore, by using the same green approach, we were also able to synthesize thiocarbonates bearing interesting functionalities. We report an efficient, fast, and environmentally friendly method for the synthesis of thiol esters starting from diorganoyl disulfides and acyl chlorides, and using CuO nanoparticles and [pmim]Br as the reductive system. This approach gave good to excellent isolated yields of the desired products in only three minutes under microwave irradiation. Copyright
- Azeredo, Juliano B.,Godoi, Marcelo,Schwab, Ricardo S.,Botteselle, Giancarlo V.,Braga, Antonio L.
-
supporting information
p. 5188 - 5194
(2013/11/06)
-
- Tetraethylammonium bromide-catalyzed oxidative thioesterification of aldehydes and alcohols
-
A metal-free, tetraethylammonium bromide-catalyzed oxidative coupling of aldehydes or alcohols with thiophenols or disulfides has been developed. This protocol affords an efficient and inexpensive approach to the synthesis of a wide range of thioesters in high yields. Copyright
- Zhu, Xuebin,Shi, Yan,Mao, Haibin,Cheng, Yixiang,Zhu, Chengjian
-
supporting information
p. 3558 - 3562
(2014/01/06)
-
- Pd-catalyzed thiocarbonylation with stoichiometric carbon monoxide: Scope and applications
-
A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)2 and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.
- Burhardt, Mia N.,Taaning, Rolf H.,Skrydstrup, Troels
-
supporting information
p. 948 - 951
(2013/03/28)
-
- Zn in ionic liquid: An efficient reaction media for the synthesis of diorganyl chalcogenides and chalcogenoesters
-
A straightforward and efficient methodology is described to synthesize structurally diverse diorganyl selenides, sulfides, seleno- and thioesters by using commercially available Zn dust in ionic liquid. Excellent yields were achieved under neutral conditions at room temperature in a short time. The solvent/ionic liquid is reusable and exhibited higher performance as compared with organic solvents.
- Narayanaperumal, Senthil,Alberto, Eduardo E.,Gul, Kashif,Kawasoko, Cristiane Yuriko,Dornelles, Luciano,Rodrigues, Oscar E.D.,Braga, Antonio Luiz
-
experimental part
p. 4723 - 4730
(2011/06/27)
-
- Bimetallic system for the synthesis of diorganyl selenides and sulfides, chiral β-seleno amines, and seleno- and thioesters
-
The bimetallic reagent Sn(II)/Cu(II) in [bmim]BF4 was efficiently used for the cleavage of diaryl diselenides and disulfides and reacts with a variety of organic substrates, such as organic halides, acid chlorides, and β-amino mesylates affording the diorganyl selenides and sulfides within very short reaction times, under mild conditions and with excellent yields, using BMIM-BF4 as a reusable solvent.
- Gul, Kashif,Narayanaperumal, Senthil,Dornelles, Luciano,Rodrigues, Oscar E.D.,Braga, Antonio Luiz
-
supporting information; experimental part
p. 3592 - 3596
(2011/07/31)
-
- Ionic liquid: An efficient and reusable media for seleno- and thioester synthesis promoted by indium
-
A series of thio and selenoesters were efficiently obtained employing stable diorganyl chalcogenides, acyl chlorides, and In as reducing agent in BMIM·PF6. Recycling of the ionic liquid was also performed, which was reused three times.
- Tabarelli, Greice,Alberto, Eduardo E.,Deobald, Anna M.,Marin, Graciane,Rodrigues, Oscar E.D.,Dornelles, Luciano,Braga, Antonio L.
-
experimental part
p. 5728 - 5731
(2010/11/16)
-
- A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite
-
Rongalite promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions.
- Dan, Weixing,Deng, Hongjuan,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
-
experimental part
p. 7384 - 7388
(2010/10/02)
-
- Effect of nucleophile on the activation parameters of transesterification of 4-nitrophenyl benzoates
-
Activation parameters of the reaction of 4-nitrophenyl benzoates with benzenethiol in the presence of potassium carbonate in dimethylformamide were determined. The entropies of activation for the reactions of unsubstituted 4-nitrophenyl benzoate and 4-nit
- Os'kina,Vlasov
-
scheme or table
p. 326 - 330
(2010/09/12)
-
- Transition-metal-catalyzed regioselective aroyl- and trifluoro- acetylthiolation of alkynes using thioesters
-
Intermolecular CO-retained carbothiolation of alkynes using thioesters took place to afford β-SR substituted enone derivatives; the choice of catalyst (Pd(dba)2-dppe) and the introduction of a CF3 group into the thioesters are the key to achieving the transformation. The Royal Society of Chemistry 2009.
- Minami, Yasunori,Kuniyasu, Hitoshi,Miyafuji, Kiyoshi,Kambe, Nobuaki
-
experimental part
p. 3080 - 3082
(2009/12/01)
-
- Kinetics of the reaction of substituted 4-nitrophenyl benzoates with benzenethiol in the presence of potassium carbonate in dimethylformamide
-
The effect of the substituent nature on the rate and activation parameters of transesterification of a series of 4-nitrophenyl benzoates with benzenethiol in dimethylformamide in the presence of potassium carbonate was studied by the competing reaction method. In all cases, change of the Gibbs energy of activation is determined mainly by variation of the enthalpy of activation. 4-Nitrophenyl benzoates having electron-withdrawing substituents in the benzoyl fragment were found to fit an isokinetic relation with an isokinetic temperature β of 318 K. Enthalpy-entropy compensation effect was observed in the reactions with all the examined 4-nitrophenyl benzoates. The relation between the reactivity and polarizability of nucleophilic center in S-and O-nucleophiles is discussed.
- Os'kina,Vlasov
-
experimental part
p. 561 - 569
(2009/04/05)
-
- Palladium-catalyzed thiocarbonylation of iodoarenes with thiols in phosphonium salt ionic liquids
-
(Chemical Equation Presented) Trihexyl(tetradecyl)phosphonium hexafluorophosphate, a phosphonium salt ionic liquid (PSIL) is a particularly effective general reaction media for the Pd-catalyzed carbonylation reaction of iodoarenes and thiols to form thioesters. Recycling of the ionic liquid containing active Pd-catalyst was also demonstrated.
- Cao, Hong,McNamee, Laura,Alper, Howard
-
p. 3530 - 3534
(2008/09/20)
-
- Dess-Martin periodinane mediated synthesis of thioesters from aldehydes
-
Dess-Martin periodinane (DMP) mediated efficient synthesis of thioesters from the corresponding aldehydes under mild conditions is described.
- Bandgar, Sunita B.,Bandgar,Korbad,Sawant
-
p. 1287 - 1290
(2007/10/03)
-
- Hypervalent iodine in synthesis 56: A convenient route for the synthesis of thiol esters via palladium-catalysed alkylthiocarbonylation or arylthio-carbonylation of diaryliodonium salts
-
Palladium-catalysed alkylthiocarbonylation or arylthiocarbonylation of diaryliodonium salts gives thiol esters in good yields.
- Wang,Chen
-
p. 372 - 373
(2007/10/03)
-
- Sulfide Oxidation and Oxidative Hydrolysis of Thioesters by Peroxymonosulfate Ion
-
Peroxymonosulfate ion, HSO5-, as OXONE, in aqueous MeCN readily converts aryl thiobenzoates, XC6H4CO*SC6H4Z (X = p-OMe, p-Me, H, p-Cl, p-CN; Z = p-OMe, p-Me, H, m-OMe, p-Cl, m-Cl, p-NO2) into carboxylic and sulfonic acids.Reactions are second order and have small substituent effects, with ρ ca. -0.6 based on ?m and ?p substituent parameters, but rates increase markedly with increasing water content in aqueous MeCN and entropies of activation are negative.The initial step is very similar to the oxidation of methyl aryl sulfides by HSO5- which has similar solvent and substituent effects.Enthalpies of activation are much lower for oxidation of the sulfides than of the corresponding esters but entropies of activation are similar.
- Bunton, Clifford A.,Foroudian, Houshang J.,Kumar, Anurag
-
-
- A Novel Method of Synthesis of 2-Methylthio-1,3-oxazoles
-
A one-pot synthesis of 2-methylthio-1,3-oxazoles by a cyclocondensation reaction between dimethyl N-(ethoxycarbonylmethyl)iminodithiocarbonate and S-phenyl alkanethioates and thiobenzoates is described.The new procedure offers several advantages: easy access of the reagents, high selectivity, and facile introduction of different substitutions in the heterocyclic ring.
- Alvarez-Ibarra, Carlos,Mendoza, Magnolia,Orellana, Guillermo,Quiroga, Maria L.
-
p. 560 - 562
(2007/10/02)
-