- Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides
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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
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p. 739 - 749
(2021/01/09)
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- Methanesulfonic anhydride-promoted sustainable synthesis of thioesters from feedstock acids and thiols
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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.].
- Singh, Pallavi,Peddinti, Rama Krishna
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- Harnessing the catalytic behaviour of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP): An expeditious synthesis of thioesters
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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.
- Singh, Pallavi,Peddinti, Rama Krishna
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supporting information
p. 1875 - 1878
(2017/04/21)
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- Formation of C(sp2)-S bonds through decarboxylation of α-oxocarboxylic acids with disulfides or thiophenols
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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
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p. 26461 - 26464
(2015/03/30)
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- Catalyst-free direct decarboxylative coupling of α-keto acids with thiols: a facile access to thioesters
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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
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p. 7323 - 7330
(2015/07/01)
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- Polymer supported Pd catalyzed thioester synthesis via carbonylation of aryl halides under phosphine free conditions
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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
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p. 26181 - 26192
(2014/07/08)
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- Pd-catalyzed thiocarbonylation with stoichiometric carbon monoxide: Scope and applications
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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
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supporting information
p. 948 - 951
(2013/03/28)
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- A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite
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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
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experimental part
p. 7384 - 7388
(2010/10/02)
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- Rapid and regiospecific phenylthiolation of some organic acids catalyzed by AlCl3 in the presence of excess anhydrous ZnCl2
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Phenylthiolation of some carboxylic acids catalyzed by AlCl3 in the presence of excess dehydrating agent (ZnCl2) has been achieved. Moreover, regiospecificity was tested of some dioic acids and found to be specific at the aliphatic p
- Roy,Sarker, Ashis K.,Mamun, A. H. Al
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experimental part
p. 2158 - 2163
(2010/08/13)
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- Oxidation of 1-[(Aryl)(phenylseleno)methyl]-, 1-[(Aryl)(arylthio)-(phenylseleno)methyl]-, and 1-[(Aryl)(diphenylseleno)-methyl]benzotriazoles with m-Chloroperbenzoic Acid
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During the last decade, benzotriazole (1) has received much attention as an excellent synthetic auxiliary [1]. Recently Katritzky, et al. [2] studied the oxidation of 1-(phenylthiomethyl)benzotriazole (2a) and 1-(2-phenyl-1-phenylthioethyl)benzotriazole (2b) and obtained their sulfones and sulfoxides by treatment with m-chloroperbenzoic acid (m-CPBA) and sodium periodate, respectively. No compounds derived from a heterolytic cleavage between the α-carbon and the N-1 atoms of the foregoing compounds were isolated.
- Kang, Yoon Ho,Kim, Kyongtae
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p. 1741 - 1752
(2007/10/03)
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