- 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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- Synthesis of selenol esters via the reaction of acyl chlorides with diselenides in the presence of Zn dust catalyzed by CoCl2·6H2O
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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.
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supporting information
(2021/08/25)
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- Preparation method of thioester compounds
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The invention discloses a preparation method of thioester compounds, wherein the method comprises the following steps: adding nickel trifluoromethanesulfonate, 4,4'-di-tert-butyl-2,2'-dipyridyl, carbonyl molybdenum, potassium carbonate, zinc iodide, water
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Paragraph 0036-0047; 0060-0061
(2021/01/29)
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- Visible-Light-Mediated Cross Dehydrogenative Coupling of Thiols with Aldehydes: Metal-Free Synthesis of Thioesters at Room Temperature
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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
- Roy, Vishal Jyoti,Sen, Partha Pratim,Raha Roy, Sudipta
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p. 16965 - 16976
(2021/11/18)
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- Nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy
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Herein reported is a nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy by using simple and readily available thioesters. In contrast to traditional activation of weaker C(acyl)-S bond, the C(acyl)-C bond of
- Feng, Yunxia,Yang, Shimin,Zhao, Shen,Zhang, Dao-Peng,Li, Xinjin,Liu, Hui,Dong, Yunhui,Sun, Feng-Gang
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supporting information
p. 6734 - 6738
(2020/09/15)
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- Nickel-Catalyzed Thiocarbonylation of Arylboronic Acids with Sulfonyl Chlorides for the Synthesis of Thioesters
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An interesting procedure for thioester synthesis via nickel-catalyzed thiocarbonylation of arylboronic acid with sulfonyl chlorides as the sulfur source has been explored. Using Mo(CO)6 as a solid CO surrogate and reductant, a broad range of thioesters were obtained in moderate to good yields with good functional group tolerance.
- Qi, Xinxin,Bao, Zhi-Peng,Yao, Xin-Tong,Wu, Xiao-Feng
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supporting information
p. 6671 - 6676
(2020/09/02)
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- Air-Tolerant Direct Thiol Esterification with Carboxylic Acids Using Hydrosilane via Simple Inorganic Base Catalysis
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Direct thioesterification of carboxylic acids with thiols using nontoxic activation agents is highly desirable. Herein, an efficient and practical protocol using safe and inexpensive industrial waste polymethylhydrosiloxane as the activation agent and K3PO4 with 18-crown-6 as a catalyst is described. Various functional groups on carboxylic acid and thiol substituents can be tolerated by the present system to afford thioesters in yields of 19-100%.
- Xuan, Maojie,Lu, Chunlei,Liu, Meina,Lin, Bo-Lin
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p. 7694 - 7701
(2019/06/27)
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- One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions
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In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.
- Liao, Yen-Sen,Liang, Chien-Fu
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p. 1871 - 1881
(2018/03/23)
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- Method for Producing Carboxylic Acid Thioester
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According to the present invention, there is provided a method for producing carboxylic acid thioester, comprising reacting a compound represented by the following formula (I), carboxylic acid and thiol in the presence of a catalyst including at least one Group 2 metal compound. The production method is a production method which is simple in reaction operation, which places a small load on the environment and the human body and which enables carboxylic acid thioester to be catalytically obtained at a high yield even at a normal temperature and a normal pressure (25° C., 1 atm). In the formula (I), R1 and R2 each independently represent a hydrocarbon group having 1 to 20 carbon atoms.
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Paragraph 0077-0083
(2018/11/02)
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- Microwave-assisted direct thioesterification of carboxylic acids
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A one-pot synthesis of thioesters directly from carboxylic acids, N,N′-diphenylthiourea, triethylamine, and primary alkyl halides is described. Microwave-assisted heating and a catalytic amount of 4- (dimethylamino)pyridine (DMAP) further improved the yields. Both aromatic and aliphatic carboxylic acids were converted to the corresponding thioesters, and many functional groups were compatible with this reaction. Several possible reaction intermediates were investigated, and the quaternary ammonium salts, derived from alkyl halides and tertiary amines, were the intermediates to yield thioesters. A new reaction mechanism for this thioesterification is proposed.
- Chou, Yen-Lin,Jhong, Yi,Swain, Sharada Prasanna,Hou, Duen-Ren
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p. 10201 - 10208
(2018/05/31)
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- Ligand-Controlled Divergent Cross-Coupling Involving Organosilicon Compounds for Thioether and Thioester Synthesis
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A divergent cross-coupling for both thioether and thioester construction from organosilicon compounds has been developed. Predominant selectivity for Hiyama-type coupling and C1 insertion reaction was achieved under the guidance of ligands. Thioether was obtained under ligand-free conditions in which disulfide generated from homocoupling could be prevented. Meanwhile, application of bidentate phosphine ligands under carbon monoxide atmosphere (CO balloon) afforded the thioester with little decomposition, which was revealed through interval NMR tracking.
- Qiao, Zongjun,Jiang, Xuefeng
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supporting information
p. 1550 - 1553
(2016/05/02)
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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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- A novel nickel-catalyzed synthesis of thioesters, esters and amides from aryl iodides in the presence of chromium hexacarbonyl
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This study describes our findings on a novel and cheap NiCl2 catalytic system under ligand-free conditions for the efficient thiocarbonylation, alkoxycarbonylation and amidocarbonylation reactions of aryl iodides in the presence of Cr(CO)6 as the solid source of carbon monoxide under air. A variety of aryl iodides tolerated the reaction conditions and structurally different thiols, alcohols and amines were used efficiently. The corresponding thioesters, esters and amides were obtained in good to excellent yield at atmospheric pressure under mild reaction conditions.
- Iranpoor, Nasser,Firouzabadi, Habib,Etemadi-Davan, Elham,Nematollahi, Arash,Firouzi, Hamid Reza
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p. 6445 - 6452
(2015/08/11)
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- Metal-free cross-coupling reaction of aldehydes with disulfides by using DTBP as an oxidant under solvent-free conditions
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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
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p. 2644 - 2652
(2014/05/06)
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- Coenzyme-inspired chemistry 2: 4,5-dihydroimidazolium ylides (NHCs) and the reactions of 2-(1-hydroxyalkyl)-4,5-dihydroimidazoles
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Ketones are prepared from aldehydes via 1-benzyl-2-(1-hydroxyalkyl)-4,5- dihydroimidazoles (adducts of the aldehydes with 1-benzyl-2-lithio-4,5- dihydroimidazoles) whereas 1-benzyl-2-(1-oxoalkyl)-4,5-dihydroimidazoles are shown to act as acyl transfer reagents via C-C bond cleavage. 4,5-Dihydroimidazolium ylides (NHCs) are intermediates in both processes, which constitute thiamine-inspired C-C bond formation and cleavage protocols.
- Jones, Raymond C. F.,Nichols, John R.
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p. 5926 - 5935
(2013/09/12)
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- Base-induced mechanistic variation in palladium-catalyzed carbonylation of aryl iodides
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A mechanism, which is distinct from the traditional one when sodium alkoxide was used instead of tertiary amines, was proposed for the alkoxycarbonylation of aryl iodides. The catalytic cycle was composed of oxidative addition, subsequent ArPdOR formation, CO insertion to Pd-OR, and final reductive elimination of ArPdCOOR. The kinetic simultaneity of the formation of deiodinated side product from the aryl iodide and aldehyde from corresponding alcohol provided strong evidence for the existence of ArPdOR species. The observation of thioether, as the other competitive product in palladium catalyzed thiocarbonylation of aryl iodides and sodium alkylthiolate, also indicate the possibility of metathesis between ArPdl and sodium alkylthiolate. Preliminary kinetic studies revealed that neither oxidative addition nor reductive elimination was rate limiting. DFT calculation displayed preference for CO insertion into Pd-OR bond. The advantage of this novel mechanism had been demonstrated in the facile alkoxycarbonylation and thiocarbonylation. The ethoxycarbonylation of aryl iodides under room temperature and balloon pressure of CO in the presence of EtONa were examined, and good to high yields were obtained; the t-butoxycarbonylation reactions in the presence of t-BuONa were achieved, and the alkylthiocarbonylation (including the t-butylthiocarbonylation) of aryl iodides in the presence of sodium alkylthiolate were also investigated.
- Hu, Yanhe,Liu, Jing,Lu, Zhixin,Luo, Xiancai,Zhang, Heng,Lan, Yu,Lei, Aiwen
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supporting information; experimental part
p. 3153 - 3158
(2010/05/15)
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- Ionic liquid as catalyst and reaction medium: A simple, convenient and green procedure for the synthesis of thioethers, thioesters and dithianes using an inexpensive ionic liquid, [pmIm]Br
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An easily accessible and inexpensive room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes the reaction of alkyl halides or acyl halides with thiols without any solvent at room temperature leading to the synthesis of thioethers and thioesters in high yields. This reaction has also been extended for the preparation of dithianes and transthioetherification. The ionic liquid is recovered and recycled for subsequent runs.
- Ranu, Brindaban C.,Jana, Ranjan
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p. 1811 - 1818
(2007/10/03)
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- High-load, soluble oligomeric carbodiimide: Synthesis and application in coupling reactions
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A facile preparation of a high-load, soluble oligomeric alkyl cyclohexylcarbodiimide (OACC) reagent via ROM polymerization from commercially available starting materials is described. This reagent is exploited as a coupling reagent for esterification, amidation, and dehydration of carboxylic acids (aliphatic and aromatic) with an assortment of alcohols (aliphatic primary, secondary, and benzylic), thiols, phenols, and amines (aliphatic primary, secondary, benzylic, and aromatic/anilines), respectively. Following the coupling event, precipitation with an appropriate solvent (Et2O, MeOH, or EtOAc), followed by filtration through a SPE provides the products in good to excellent yield and purity.
- Zhang, Mianji,Vedantham, Punitha,Flynn, Daniel L.,Hanson, Paul R.
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p. 8340 - 8344
(2007/10/03)
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- High-Load, ROMP-Generated Oligomeric Bis-acid Chlorides: Design of Soluble and Insoluble Nucleophile Scavengers
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(Equation presented) An efficient strategy for scavenging a host of nucleophiles utilizing an oligomeric bis-acid chloride (OBAC), generated from the ROM polymerization of trans-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonyl dichloride, is described. The reactivity and high load of the OBAC reagent is exploited in the scavenging of amines, alcohols, and thiols that are present in excess following a common benzoylation event. Following the scavenging event, these oligomers can be precipitated with EtOAc and filtered (SiO2), leaving benzoylated nucleophiles in excellent yield and purity.
- Moore, Joel D.,Byrne, Robert J.,Vedantham, Punitha,Flynn, Daniel L.,Hanson, Paul R.
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p. 4241 - 4244
(2007/10/03)
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- Convenient synthesis of thiol esters from acyl chlorides and disulfides using Zn/AlCl3
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Various thiol esters were prepared by condensation of acyl chlorides with disulfides in the presence of Zn/AlCl3. The advantages of this method are high yields under relatively mild conditions, simple work-up, lack of toxicity, and low costs.
- Lakouraj, Moslem M.,Movassagh, Barahman,Fadaei, Zahra
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p. 1085 - 1088
(2007/10/03)
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- NEW CONDENSING REAGENTS: THIOPHOSPHORUS COMPOUNDS ACTIVATED BY 2-OXAZOLONE AND 2-BENZOXAZOLINONE HETEROCYCLES
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The thiophosphorus compounds (3-6) activated by 2-oxazolone and 2-benzoxazolinone heterocycles, which have the advantages of high solubility in organic solvents and good preservability, serve well as versatile condensing reagents for one-step formation of amides including β-lactams, esters and thioesters from carboxylic acids.
- Otsubo, Teruyuki,Matsukawa, Chiyoko,Ishizuka, Tadao,Kunieda, Takehisa
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p. 131 - 134
(2007/10/02)
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- Thiamine coenzyme models: Imidazolinium ylides and the reactions of 2-(hydroxyalkyl)imidazolines
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Ketones are prepared from aldehydes via 1-benzyl-2-(1-hydroxyalkyl)-2-imidazolines (adducts of the aldehydes with 1-benzyl-2-lithio-2-imidazoline) whereas 1-benzyl-2-(1-oxoalkyl)-2-imidazolines act as acyl transfer reagents; imidazolinium ylides are intermediates in both processes.
- Jones, Raymond C. F.,Nichols, John R.
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p. 1771 - 1774
(2007/10/02)
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- A Novel Synthesis of Thiocarboxylic S-Esters from 1-(Acylthio)ethaniminium Halides and Alkyl Halides Using Liquid-Liquid Phase-Transfer Catalysis
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S-Alkyl, S-benzyl, and S-(2-alkenyl) thiocarboxylates are prepared in good yields by acylation of thioacetamide with acyl halides and reaction of the resultant 1-(acylthio)ethaniminium halides with alkyl halides under liquid-liquid phase-transfer conditions.
- Takido, Toshio,Toriyama, Masaharu,Itabashi, Kunio
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p. 404 - 406
(2007/10/02)
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- THIOALKYLTRIBUTYL- AND THIOALKOXYTRIPHENYLPHOSPHONIUM SALTS: PREPARATION AND APPLICATION TO THE SYNTHESIS OF THIOLESTERS AND UNSYMMETRICAL SULFIDES
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Thioalkoxyphosphonium salts, Ph3PSR(1+)*ClO4(1-) (3) and Bu3PSR(1+)*X(1-) (X=ClO4 and BF4) (5), have been prepared from the corresponding tertiary phosphines and disulfides by simple procedures, which involve (i) constant current electrolysis in acetonitrile in the presence of either HClO4 (for 3) or PhCOOH and LiX (for 5), and (ii) stirring an equimolar mixture of a phosphine, a disulfide, PHCOOH, and LiX in acetonitrile at ambient temperature.For the preparation of 3, which have been reported as useful reagents for the synthesis of unsymmetrical disulfides, the electrochemical method is recomended, while for 5 the latter non-electrochemicl procedure gave better results.Reactions of the phosphonium salts 5 with carboxylic acidsand primary alcohols in benzene at ambient temperature gave thiolesters and unsymmetrical sulfides, respectively, in fair to excellent yields.Keywords - triphenylphosphine; tributylphosphine; disulfide; thioalkoxyphosphonium salt; thiolester; unsymmetrical sulfide
- Ohmori, Hidenobu,Maeda, Hatsuo,Konomoto, Kohichi,Sakai, Kiyoshi,Masui, Masaichiro
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p. 4473 - 4481
(2007/10/02)
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- DI-2-PYRIDYL CARBONATE: A NEW EFFICIENT COUPLING AGENT FOR THE DIRECT ESTERIFICATION OF CARBOXYLIC ACIDS
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Reaction of carboxylic acids with equimolar amounts of di-2-pyridyl carbonate and alcohols or thiols in the presence of 4-dimethylaminopyridine as a catalyst in methylene chloride at room temperature affords the corresponding esters in high yields under mild conditions.
- Kim, Sunggak,Lee, Jae In,Ko, Young Kwan
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p. 4943 - 4946
(2007/10/02)
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- A FACILE PREPARATION OF THIOL ESTERS FROM CARBOXYLIC ACIDS AND THIOLS
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Thiol esters can be conveniently prepared by the reaction of carboxylic acids with thiols and 1-fluoro-2,4,6-trinitrobenzene in the presence of 4-dimethylaminopyridine.The thiol ester formation is found to be very effective for simple carboxylic acids.
- Kim, Sunggak,Yang, Sungbong
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p. 133 - 134
(2007/10/02)
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- EFFICIENT CONVERSION OF CARBOXYLIC ACIDS INTO THIOL ESTERS
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A facile and direct preparation of thiol esters from carboxylic acids and thiols using diphenyl 2-oxo-3-oxazolinylphosphonate in the presence of triethylamine is described.
- Kunieda, Takehisa,Abe, Yoshihiro,Hirobe, Masaaki
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p. 1427 - 1428
(2007/10/02)
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- The Conversion of Amino into Sulphur Functionality
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Primary alkylamines are converted by pyryliums into pyridiniums, which transfer their N-substituents to various sulphur nucleophiles.
- Katritzky, Alan R.,Rezende, Marcos C.,Thind, Sukhpal S.
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p. 4031 - 4040
(2007/10/02)
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- Transacylations with Acyl Derivatives of 4-Pyridones
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Aliphatic and aromatic amines as well as thiols react with N-acyl-4-pyridones (2a, b) and with 4-(benzoyloxy)pyridine (3a) in methylene chloride or chloroform to give the N-substituted amides 4-6 and the thiol esters 7 and 8, respectively, with very good yields.Primary and secondary alcohols react more slowly, tert-butyl alcohol only with 3a to the tert-butyl esters 12 under basic catalysis or with the much more reactive N-(trihaloacetyl)-4-pyridones 3b, c.N-Acetyl-4-pyridone (2a) possesses a much higher acylation potential than N-acetylimidazole (13a).
- Effenberger, Franz,Bessey, Eberhard
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p. 2100 - 2109
(2007/10/02)
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