- Indium(III)-catalysed highly regioselective addition of thiolacetic acid to non-activated olefins
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Indium(III) chloride and indium(III) trifluoromethanesulfonate were found to be excellent catalysts for the addition of thiolacetic acid to non-activated olefins. The reaction is highly regioselective and can be run in the presence of 1 mol % of catalyst.
- We?wer, Michel,Du?ach, Elisabet
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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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- P2O5/Al2O3 AS an efficient heterogeneous catalyst for the acetylation of alcohols, phenols, thiols, and amines under solvent-free conditions
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A convenient, rapid, and efficient method for the acetylation of alcohols, phenols, thiols, and amines has been developed by using acetic anhydride in the presence of a catalytic amount of P2O5/Al 2O3 under solvent-free conditions at room temperature. This reaction was studied under different conditions, and several solvents were examined for this conversion. However, in terms of reaction time and yield, it was found that the best result was obtained when the reaction was carried out under solvent-free conditions. Racemization of optically active alcohols and epimerization of sugars were not observed. The use of nontoxic and inexpensive materials, simple and clean workup, short reaction times, and good yields of the products are the advantages of this method.
- Zarei, Amin,Hajipour, Abdol R.,Khazdooz, Leila
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- Lewis acid catalyzed acylation reactions: Scope and limitations
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Acylation of alcohols, thiols, and sugars were studied with a variety of Lewis acids, and it was found that Cu- and Sn(OTf)2 are very efficient in catalyzing the reaction under mild conditions. Among these two catalysts, Cu(OTf)2 was preferred because of its lower cost and relatively higher yield of the acylated product. The reaction was studied in several solvents, but CH2Cl2 was preferred. It was also observed that the present method is suitable for acylation of tertiary alcohols. Sugars were also acylated without any epimerization at the anomeric center. It is further shown here that this method is also suitable for selective acylation of primary or secondary alcohols over tertiary ones.
- Chandra, Kusum L,Saravanan,Singh, Rajesh K,Singh, Vinod K
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- Poly-(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide) and N,N,N′,N′- tetrabromobenzene-1,3-disulfonamide as highly efficient catalysts, and (AC2O/SIO2) as a heterogeneous system for the acetylation of alcohols, amines, and thiols under microwave irradiation
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Chemical Equation Presented Poly-(N,N′-dibromo-N-ethyl-benzene-1,3- disulfonamide) (PBBS) and N,N,N′,N′-tetrabromobenzene-1,3- disulfonamide (TBBDA) are good activators and catalytic reagents for the acetylation of alcohols, amines, and thiols. The presented method has the advantages of mild conditions, chemoselectivity, and good to high yields, and uses noncorrosive, inexpensive, recyclable, and environmentally friendly catalysts. We have also demonstrated that combining SiO2 with microwave energy provides an efficient, fast, convenient, and easy workup procedure for the synthesis of mono- and disubstituted acetates, acetamides, and thioacetamides. Copyright Taylor & Francis Group, LLC.
- Veisi, Hojat,Ghorbani-Vaghei, Ramin,Eskandari, Hosna,Hemmati, Saba,Rezaei, Ardashir,Hajinazari, Somaye,Far, Mohammad Raoof Heidari,Entezari, Azam
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- Tris(pentafluorophenyl)borane catalyzed acylation of alcohols, phenols, amines, and thiophenols under solvent-free condition
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The acylation of alcohols, phenols, amines, and thiophenols was accomplished with 0.5 mol % of tris(pentafluorophenyl)borane [B(C 6F5)3] at ambient temperature under solvent-free condition. Major advantages of this method include high yield, short reaction time, simple procedure, compatibility with sensitive protecting groups as well as other functional groups, absence of racemization of optical active compounds, and epimerization of sugars.
- Prajapti, Santosh Kumar,Nagarsenkar, Atulya,Babu, Bathini Nagendra
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- Mild Ti-mediated transformation of t-butyl thio-ethers into thio-acetates
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We report a straightforward method for the rapid conversion of thio-ethers to thio-acetates using TiCl4, in good to excellent yields. The reaction conditions tolerate a variety of functional groups, including halide, nitro, ether, thiophene and acetylene functionalities. A catalytic variant of this reaction is also described. This journal is
- Pijper, Thomas C.,Robertus, Jort,Browne, Wesley R.,Feringa, Ben L.
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- Noncross-linked polystyrene nanoencapsulation of ferric chloride: A novel and reusable heterogeneous macromolecular Lewis acid catalyst toward selective acetylation of alcohols, phenols, amines, and thiols
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Ferric chloride has been successfully nanoencapsulated for the first time on a non-cross-linked polystyrene matrix as the shell material via the coacervation technique. The resulting polystyrene nanoencapsulated ferric chloride was used as a novel and rec
- Alinejad, Sara,Donyapeyma, Ghazaleh,Rahmatpour, Ali
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- Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes
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A mild, metal-free, atmospheric oxygen-mediated radical hydrothiolation of alkenes (and alkyne) is reported. A variety of sulfur containing motifs including alkanethiols, thiophenols and thioacids undergo an atmospheric oxygen-mediated radical hydrothiolation reaction with a plethora of alkenes in good yield with excellent functional group compatibility, typically with short reaction times to furnish a range of functionalized products. Biomolecules proved tolerant to the conditions and the procedure is robust and easily executable requiring no specialized equipment. Concise mechanistic studies confirm the process proceeds through radical intermediates in a thiol-ene reaction manifold. The methodology offers an efficient “green” approach for thiol-ene mediated “click” ligation and a milder alternative to thermally initiated hydrothiolation processes.
- McCourt, Ruairí O.,Scanlan, Eoin M.
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supporting information
p. 15804 - 15810
(2020/10/26)
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- Visible-Light-Mediated Organocatalyzed Thiol-Ene Reaction Initiated by a Proton-Coupled Electron Transfer
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A convenient method for performing a thiol-ene reaction is described. The reaction is performed under blue-light irradiation and catalyzed by photoactive Lewis basic molecules such as acridine orange or naphthalene-fused N-acylbenzimidazole. It is believed that the process is initiated by a proton-coupled electron transfer process within the complex between the thiol and the Lewis basic catalyst.
- Levin, Vitalij V.,Dilman, Alexander D.
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p. 8337 - 8343
(2019/06/27)
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- S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters
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This paper demonstrates an efficient, mild, and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acetylating agent. During our tests, we also investigated the differences between the activities of metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion as a heterogeneous catalyst for S-acetylation of thiols.
- Kuciński, Krzysztof,Hreczycho, Grzegorz
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p. 489 - 493
(2018/04/27)
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- In situ generated Ph3P(OAc)2as a novel reagent for the efficient acetylation of alcohols and thiols at room temperature
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Ph3P, Br2, and ammonium acetate are used for the in situ generation of Ph3P(OAc)2, which was characterized by different NMR techniques. The Ph3P(OAc)2generated was used as a novel and efficient reagent for the acetylation of alcohols and thiols in acetonitrile at room temperature under homogeneous conditions. This reaction was also performed under heterogeneous conditions using 1,3,2,4- diazadiphosphetidine as an easily prepared, stable, and heterogeneous P(III) compound.
- Iranpoor, Nasser,Firouzabadi, Habib,Elham, Etemadi Davan
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p. 1813 - 1816
(2013/04/24)
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- Solvent-free acetylation of thiols under catalysis of MgBr 2·OEt2
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Solvent-free protection of aromatic and aliphatic thiols with acetic anhydride was performed at room temperature under trace quantities of magnesium bromide ethyl etherate, affording rapid formation of various thiol esters in excellent yields. Copyright Taylor & Francis Group, LLC.
- Mojtahedi, Mohammad M.,Abaee, M. Saeed,Javadpour, Mashal
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experimental part
p. 2362 - 2365
(2011/02/22)
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- Flavouring and odorant thiols from renewable natural resources by InIII-catalysed hydrothioacetylation and lipase-catalysed solvolysis
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A chemoenzymatic access to thiol compounds, including ethyl 3-thiobutanoate, 3-thio-p-menthene and 8-thio-p-menthan-2-one, three compounds of interest in flavour and fragrance chemistry presenting various fruity notes, is proposed. It involves an indium(III)-catalysed hydrothioacetylation of renewable precursors followed by an enzymatic solvolysis of the obtained thioesters by lipases in aqueous or organic solvents.
- Dia, Reine-Marie,Belaqziz, Rim,Romane, Abderrahmane,Antoniotti, Sylvain,Du?ach, Elisabet
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supporting information; experimental part
p. 2164 - 2167
(2010/06/13)
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- Al(OTf)3 as a highly efficient catalyst for the rapid acetylation of alcohols, phenols and thiophenols under solvent-free conditions
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Aluminium triflate (0.01-0.1 mol %) was found to be an efficient catalyst for the acylation of alcohols, phenols, thiols and sugars with acetic anhydride in high yields under solvent-free conditions in a short reaction time at room temperature. Racemization of optically active alcohols and epimerization of sugars were not observed. The acylation efficacy of various acyl donors was also investigated.
- Kamal, Ahmed,Khan, M. Naseer A.,Reddy, K. Srinivasa,Srikanth,Krishnaji
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p. 3813 - 3818
(2008/02/06)
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- Practical preparation of esters and thioacetates from alkyl halides and carboxylates or thioacetate catalyzed by PEG400 without solvent
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Carboxylic esters and thioacetates were conveniently prepared in good to excellent yields under mild conditions by the reaction of alkyl halides with sodium carboxylates or sodium thioacetate catalyzed by PEG400 in the absence of solvents. Copyright Taylor & Francis Group, LLC.
- Cao, Yu-Qing,Wu, Guo-Qiang,Li, Ya-Bin,Dai, Zhi,Chen, Bao-Hua
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p. 3353 - 3358
(2007/10/03)
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- A facile and practical method for the preparation of thioacetates from alkyl halides and sodium thioacetate catalysed by PEG400
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Thioacetates are conveniently prepared in high yields under mild conditions by the reaction of alkyl halides and sodium thioacetate, prepared in situ from thioacetic acid and sodium carbonate, catalysed by PEG400 at room temperature.
- Cao, Yu-Qing,Du, Yun-Fei,Chen, Bao-Hua,Dai, Zhi
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p. 762 - 763
(2007/10/03)
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- An efficient method for acylation reactions
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Cu(OTf)2 was found to be an efficient catalyst in the acylation reaction of alcohols, phenols, amines and thiols with acetic arthydride in CH2Cl2 or acetic acid. A catalytic cycle has been proposed for the acylation reaction.
- Saravanan, Parthasarathy,Singh, Vinod K.
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p. 2611 - 2614
(2007/10/03)
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- FUNCTIONALIZATION OF SATURATED HYDROCARBONS IN THE PRESENCE OF APROTIC ORGANIC SUPERACIDS. 2. SINGLE-STAGE SYNTHESIS OF THIOESTERS R1CO-SR FROM n-ALKANES OR CYCLOALKANES (RH), ELEMENTAL SULFUR, AND COMPLEXES R1COBr*2AlBr3
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It has been found for the first time that n-alkanes and cycloalkanes (RH) can interact with elemental sulfur at ca. 20 deg C.These reactions go forward in the presence of aprotic organic superacids with the composition R1CO-SR in satisfactory yields.
- Orlinkov, A. V.,Akhrem, I. S.,Afanas'eva, L. V.,Vitt, S. V.,Vol'pin, M. E.
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- Facile Catalytic Conversion of Carboxylic Acids into Thiocarboxylic S-Acids by the Ph3SbO/P4S10 System
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Thiocarboxylic S-acids 2 are readily prepared by direct sulfuration of the corresponding carboxylic acids 1 catalyzed by Ph3SbO/P4S10 under mild conditions.
- Nomura, Ryoki,Miyazaki, Shin-Ichiro,Nakano, Takahiro,Matsuda, Haruo
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p. 2081 - 2082
(2007/10/02)
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