- Facile deallylation protocols for the preparation of N-unsubstituted triazoles and tetrazoles
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Two facile deallylation protocols have been developed for the preparation of N-unsubstituted triazoles and tetrazoles. The first protocol is a direct deallylation using a combination of a catalytic amount of nickel complex, NiCl2(dppe), and a stoichiometric amount of Grignard reagent, tBuMgCl. The second protocol is a stepwise deallylation through consecutive reactions of isomerization and ozonolysis. The isomerization from N-allylazoles to N-vinylazoles is catalyzed by a ruthenium complex, HRuCl(CO)(PPh3)3, and the following ozonolysis of the derived N-vinyl intermediates affords N-unsubstituted azoles. These protocols can be used complementarily depending on the type of functional groups in the parent allylated azoles.
- Kamijo, Shin,Huo, Zhibao,Jin, Tienan,Kanazawa, Chikashi,Yamamoto, Yoshinori
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Read Online
- Efficient synthesis of 5-substituted thiazolidin-2-ones from xanthates and tert-butyl N-allylcarbamates
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A series of 5-substituted thiazolidin-2-ones with various functional groups was synthesized efficiently via a radical addition of xanthates and tert-butyl N-allylcarbamates and subsequent 88% HCO2H-catalyzed cyclization. The mechanism of the acid-catalyzed cyclization was proposed as well.
- Huang, Zhongyan,Xu, Jiaxi
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Read Online
- Polyvinylpolypyrrolidoniume tribromide as new and metal-free catalyst for the formylation and trimethylsilylation of hydroxyl group
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Trimethylsilylation of alcohols was achieved using 1,1,1,3,3,3- hexamethyldisilazane (HMDS) as silylating agent, in the presence of polyvinylpolypyrrolidoniume tribromide in acetonitrile at room temperature. Also a variety of alcohols were converted into alkyl formates by ethyl formate and a catalytic amount of polyvinylpolypyrrolidoniume tribromide under solvent free conditions at room temperature.
- Ghorbani-Choghamarani, Arash,Goudarziafshar, Hamid,Zamani, Parisa
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Read Online
- Carbon monoxide and hydrogen (syngas) as a C1-building block for selective catalytic methylation
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A catalytic reaction using syngas (CO/H2) as feedstock for the selective β-methylation of alcohols was developed whereby carbon monoxide acts as a C1 source and hydrogen gas as a reducing agent. The overall transformation occurs through an intricate network of metal-catalyzed and base-mediated reactions. The molecular complex [Mn(CO)2Br[HN(C2H4PiPr2)2]]1comprising earth-abundant manganese acts as the metal component in the catalytic system enabling the generation of formaldehyde from syngas in a synthetically useful reaction. This new syngas conversion opens pathways to install methyl branches at sp3carbon centers utilizing renewable feedstocks and energy for the synthesis of biologically active compounds, fine chemicals, and advanced biofuels.
- Kaithal, Akash,H?lscher, Markus,Leitner, Walter
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p. 976 - 982
(2021/02/06)
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- Tandem Acid/Pd-Catalyzed Reductive Rearrangement of Glycol Derivatives
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Herein, we describe the acid/Pd-tandem-catalyzed transformation of glycol derivatives into terminal formic esters. Mechanistic investigations show that the substrate undergoes rearrangement to an aldehyde under [1,2] hydrogen migration and cleavage of an oxygen-based leaving group. The leaving group is trapped as its formic ester, and the aldehyde is reduced and subsequently esterified to a formate. Whereas the rearrangement to the aldehyde is catalyzed by sulfonic acids, the reduction step requires a unique catalyst system comprising a PdII or Pd0 precursor in loadings as low as 0.75 mol % and α,α′-bis(di-tert-butylphosphino)-o-xylene as ligand. The reduction step makes use of formic acid as an easy-to-handle transfer reductant. The substrate scope of the transformation encompasses both aromatic and aliphatic substrates and a variety of leaving groups.
- Ciszek, Benjamin,Fleischer, Ivana,Kathe, Prasad,Schmidt, Tanno A.
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p. 3641 - 3646
(2020/03/25)
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- One-Pot Conversion of Cinnamaldehyde to 2-Phenylethanol via a Biosynthetic Cascade Reaction
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A novel biosynthetic pathway for the production of natural 2-phenylethanol from cinnamaldehyde is reported. An ene-reductase (OYE)-mediated selective hydrogenation of cinnamaldehyde to hydrocinnamaldehyde is followed by a regioselective Baeyer-Villiger oxidation (BVMO) to produce the corresponding formate ester that either spontaneously hydrolyzes to 2-phenylethanol in water or is assisted by a formate dehydrogenase (FDH). This cascade reaction is performed in a one-pot fashion at ambient temperature and pressure. High selectivity and complete conversion were achieved.
- Vorster, Amanda,Smit, Martha S.,Opperman, Diederik J.
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supporting information
p. 7024 - 7027
(2019/09/12)
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- Efficient Enzymatic Preparation of Flavor Esters in Water
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A straightforward biocatalytic method for the enzymatic preparation of different flavor esters starting from primary alcohols (e.g., isoamyl, n-hexyl, geranyl, cinnamyl, 2-phenethyl, and benzyl alcohols) and naturally available ethyl esters (e.g., formate, acetate, propionate, and butyrate) was developed. The biotransformations are catalyzed by an acyltransferase from Mycobacterium smegmatis (MsAcT) and proceeded with excellent yields (80-97%) and short reaction times (30-120 min), even when high substrate concentrations (up to 0.5 M) were used. This enzymatic strategy represents an efficient alternative to the application of lipases in organic solvents and a significant improvement compared with already known methods in terms of reduced use of organic solvents, paving the way to sustainable and efficient preparation of natural flavoring agents.
- Perdomo, Igor Chiarelli,Gianolio, Stefania,Pinto, Andrea,Romano, Diego,Contente, Martina Letizia,Paradisi, Francesca,Molinari, Francesco
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p. 6517 - 6522
(2019/06/20)
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- Sustainable Co-Synthesis of Glycolic Acid, Formamides and Formates from 1,3-Dihydroxyacetone by a Cu/Al2O3 Catalyst with a Single Active Sites
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Glycolic acid (GA), as important building block of biodegradable polymers, has been synthesized for the first time in excellent yields at room temperature by selective oxidation of 1,3-dihyroxyacetone (DHA) using a cheap supported Cu/Al2O3 catalyst with single active CuII species. By combining EPR spin-trapping and operando ATR-IR experiments, different mechanisms for the co-synthesis of GA, formates, and formamides have been derived, in which .OH radicals formed from H2O2 by a Fenton-like reaction play a key role.
- Dai, Xingchao,Adomeit, Sven,Rabeah, Jabor,Kreyenschulte, Carsten,Brückner, Angelika,Wang, Hongli,Shi, Feng
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supporting information
p. 5251 - 5255
(2019/03/07)
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- Method for preparing formate-type compound
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The invention discloses a method for preparing a formate-type compound. The method comprises the following steps of: adopting an alcohol-type compound and 1,3-dihydroxyacetone as reaction raw materials, and under the existence of a composite catalyst and an oxidant, reacting for 2-48 hours in a reaction medium in a reactor at a reaction temperature of 25-100 DEG C so as to obtain the formate-typecompound. The method disclosed by the invention is simple, and is mild in reaction condition, and by the method, a target product can be obtained by low cost and high yield; the used catalyst has highcatalytic activity, and is easily separated from a reaction system to be repeatedly used; the whole process is environment-friendly, and the reaction raw material (1,3-dihydroxyacetone) is easily converted from a side product (glycerol) of biodiesel, so that the utilization of the glycerol is promoted.
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Paragraph 0039; 0047; 0048
(2018/07/30)
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- Purified mCPBA, a Useful Reagent for the Oxidation of Aldehydes
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Purified mCPBA is a useful reagent for the oxidation of several classes of aldehyde. Although linear unbranched aliphatic aldehydes are oxidized to the corresponding carboxylic acids, α-branched ones undergo Baeyer–Villiger oxidation to formates. α-Branched α,β-unsaturated aldehydes provide enolformates and/or epoxides, which can be saponified to α-hydroxy ketones with shortening of the carbon chain by 1 carbon. Unbranched α,β-unsaturated aldehydes undergo an interesting Baeyer–Villiger oxidation/epoxidation/formate migration/BV oxidation cascade, which results in formyl-protected hydrates with an overall loss of two carbon atoms.
- Horn, Alexander,Kazmaier, Uli
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p. 2531 - 2536
(2018/03/21)
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- Sulfonium Salts as Alkylating Agents for Palladium-Catalyzed Direct Ortho Alkylation of Anilides and Aromatic Ureas
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A novel method for the ortho alkylation of acetanilide and aromatic urea derivatives via C-H activation was developed. Alkyl dibenzothiophenium salts are considered to be new reagents for the palladium-catalyzed C-H activation reaction, which enables the transfer of methyl and other alkyl groups from the sulfonium salt to the aniline derivatives under mild catalytic conditions.
- Simkó, Dániel Cs.,Elekes, Péter,Pázmándi, Vivien,Novák, Zoltán
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supporting information
p. 676 - 679
(2018/02/09)
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- Application of polydopamine sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (Fe3O4@PDA-SO3H) as a heterogeneous and recyclable nanocatalyst for the formylation of alcohols and amines under solvent-free conditions
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Herein, formylation of structurally different amines and alcohols with ethyl formate was carried out in the presence of a catalytic proportion of sulfonic acid supported on polydopamine (PDA)-encapsulated Fe3O4 nanoparticles as a heterogeneous, recyclable, and greatly efficient catalyst; this method provided the corresponding N-formyl compounds in good to excellent yields under solvent-free conditions. The magnetically catalytic system was recovered, by-passing the time-consuming filtration operation using an external magnet device. This procedure also increases the purity of the product and promises economic and ecological advantages. Furthermore, the recovery and reuse of the catalyst was demonstrated five times without detectable loss in the activity.
- Taheri, Sepideh,Veisi, Hojat,Hekmati, Malak
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p. 5075 - 5081
(2017/07/11)
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- N-Heterocyclic Carbene Catalyzed Transformylation
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The N-heterocyclic carbene (NHC) catalyzed transformylation has been developed for the conversion of 1°, 2°, and 3° alcohols to the corresponding formates. The reaction employs low catalyst loadings and methyl formate as the formyl transfer reagent. The scope of the reaction is broad with 23 examples reported with good yields (59-96%). The reaction is insensitive to common nitrogen and oxygen protecting groups and can be achieved in the presence of a number of heterocycles.
- Fernando, Jared E. M.,Levens, Alison,Moock, Daniel,Lupton, David W.
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p. 3505 - 3510
(2017/07/27)
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- Tribromoisocyanuric acid (TBCA) as a mild and metal free catalyst for the acetylation and formylation of hydroxyl groups under solvent free conditions
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A convenient approach for acetylation and formylation of various types of alcohols and phenols with acetic anhydride and formic acid in the presence of Tribromoisocyanuric acid (TBCA) as catalyst is reported. The reactions were carried out under solvent-free condition and in good to high yields at room temperature. This present method is featured with relatively mild reaction conditions, simple operation, broad substrate scope, clean work-up, short reaction times, good to high yields, excellent selectivity and also avoids tedious purifications and the use of toxic reagents.
- Hekmatian, Zahra,Khazaei, Ardeshir
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p. 1565 - 1570
(2016/01/26)
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- 2-(Sulfooxy)propane-1,2,3-tricarboxylic acid as novel and versatile catalyst for the formylation of alcohols and amines using ethyl formate under neat conditions
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2-(Sulfooxy)propane-1,2,3-tricarboxylic acid (supported on silica gel) has been introduced as novel and green catalyst for the formylation of alcohols and amines with ethyl formate, as mild formylation agent, under neat conditions at room temperature.. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
- Ghorbani-Choghamarani, Arash,Akbaripanah, Ziba
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experimental part
p. 450 - 453
(2012/06/04)
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- Formylation of alcohol with formic acid under solvent-free and neutral conditions catalyzed by free I2 or I2 generated in situ from Fe(NO3)3·9H2O/NaI
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Different alcohols were formylated by formic acid under solvent-free conditions in the presence of iodine as the catalyst with good-to-high yields at room temperature. I2 generated in situ from Fe(NO3) 3·9H2O/NaI also catalyzed the formylation of the alcohols under solvent-free conditions. This gives a green and efficient reaction at room temperature, in which the use of toxic and corrosive molecular I2 is avoided.
- Amin, Rostami,Ardeshir, Khazaei,Heidar Ali, Alavi-Nik,Zahra, Toodeh-Roosta
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experimental part
p. 60 - 64
(2011/10/08)
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- Formylation of amines and alcohols using aminopropylated mesoporous SBA-15 silica (APMS) as an efficient and recyclable catalyst
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Aminopropylated mesoporous SBA-15 silica (APMS) is introduced as a new, recyclable and efficient catalyst for the formylation of a variety of amines and alcohols by using readily available formic acid under solvent-free conditions.
- Malakooti, Reihaneh,Sobhani, Sara,Razavi, Nasrin,Shafiei, Soheila,Mokhtari, Rezvan
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experimental part
p. 1979 - 1990
(2012/04/17)
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- N,N′-dibromo-N,N′-1,2-ethanediylbis(benzene sulfonamide) as an efficient catalyst for acetylation and formylation of alcohols under mild conditions
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An efficient method for the acylation and formylation of alcohols and phenols by using an acylating/formylating agent (acetic anhydride and formic acid) in the presence of a catalytic amount of N,N′-dibromo-N,N′-1, 2-ethanediylbis(benzene sulfonamide) under mild and solvent-free conditions at room temperature in good to excellent yields is described. The use of protic acids and metal Lewis acids is avoided.
- Khazaei, Ardeshir,Rostami, Amin,Rosta, Zahra,Alavi, Ali
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experimental part
p. 181 - 186
(2010/04/05)
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- P-Toluenesulfonyl chloride as a new and effective catalyst for acetylation and formylation of hydroxyl compounds under mild conditions
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The catalytic application of p-toluenesulfonyl chloride for efficient acetylation of various types of alcohols and phenols with acetic anhydride in solvent-free conditions is reported. Also structurally diverse alcohols were formylated using formic acid based on the use of catalytic amount of p-toluenesulfonyl chloride under solvent-free condition. The reactions were carried out in short reaction time and in good to excellent yields at room temperature.
- Khazaei, Ardeshir,Rostami, Amin,Mantashlo, Fatemeh
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experimental part
p. 1430 - 1434
(2011/10/08)
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- Silica-bonded N-propyl sulfamic acid as an efficient catalyst for the formylation and acetylation of alcohols and amines under heterogeneous conditions
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A simple and efficient procedure for the preparation of silica-bonded N-propyl sulfamic acid (SBNPSA) by the reaction of 3-aminopropylsilica (1) and chlorosulfonic acid in chloroform is described. This solid acid is employed as a new catalyst for the formylation of alcohols and amines with ethyl formate under mild and heterogeneous conditions at room temperature with good to excellent yields. Also, SBNPSA catalyzed acetylation of various alcohols and amines with acetic anhydride at room temperature.
- Niknam, Khodabakhsh,Saberi, Dariush
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experimental part
p. 5210 - 5214
(2009/12/06)
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- Polyethylene glycol radical-initiated oxidation of benzylic alcohols in compressed carbon dioxide
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The PEG radical from oxidative degradation of polyethylene glycol was first used to initiate the oxidation of benzylic alcohols to carbonyl compounds without the need of a catalyst and/or additive in a viable synthetic, cost-effective and environmentally benign way, in which PEG/O 2/CO2 acts as initiator, oxidant and solvent. Compressed CO2 in this study not only provides a safe environment to conduct the oxidation employing molecular oxygen as an oxidant, but also could improve the reaction and adjust the selectivity of the target product by altering CO 2 pressure. Moreover, this methodology could be used to oxidize a set of benzyl alcohols. The findings introduced here provide useful examples for developing free-radical chemistry from PEG thermal oxidative degradation.
- Wang, Jin-Quan,He, Liang-Nian,Miao, Cheng-Xia
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experimental part
p. 1013 - 1017
(2010/04/23)
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- Silica sulfuric acid and AI(HSO4)3: As efficient catalysts for the formylation of alcohols by using ethyl formate under heterogeneous conditions
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A mixture of ethyl formate and a catalytic amount of silica sulfuric acid or Al(HSO4)3 as suitable formylating systems can formylate various alcohols to their corresponding formate ester derivatives under mild, nearly neutral and heterogeneous conditions at room temperature with good to excellent yields.
- Zolfigol, Mohammad Ali,Chehardoli, Gholamabbas,Dehghanian, Mina,Niknam, Khodabakhsh,Shirini, Farhad,Khoramabadi-Zad, Ahmad
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experimental part
p. 885 - 889
(2009/12/04)
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- Efficient acetylation and formylation of alcohols in the presence of Zr(HSO4)4
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Acetylation and formylation of alcohols with acetic and formic acids have been carried out in the presence of catalytic amounts of Zr(HSO 4)4 under mild and heterogeneous conditions.
- Shirini, Farhad,Zolfigol,Safari
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p. 154 - 156
(2007/10/03)
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- Corona-induced photoxidation of alcohols and hydrocarbons over TiO 2 in the absence of a UV light source - A novel and environmentally friendly method for oxidation
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Corona-induced photooxidation is a novel oxidation methodology for the efficient oxidation of alcohols and hydrocarbons utilizing the advantage of both the high oxidizing power of ozone formed in the reactor as well as the photooxidation capability of the UV light generated during the corona discharge. The Royal Society of Chemistry 2005.
- Pillai, Unnikrishnan R.,Sahle-Demessie, Endalkachew
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p. 2256 - 2258
(2007/10/03)
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- Efficient one-step conversion of tetrahydropyranyl ethers into acetates and formates in the presence of potassium dodecatungstocobaltate K 5CoW12O40·3H2O
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Tetrahydropyranyl ethers derived from primary alcohols were directly and efficiently converted into the corresponding acetates and formates by the action of ethyl acetate, acetic acid, acetic anhydride, and ethyl formate in the presence of a catalytic amount of potassium dodecatungstocobaltate K 5CoW12O40 ? 3H2O. Tetrahydropyranyl ethers derived from secondary alcohols and phenols can also be transformed into the corresponding acetates with the use of acetic anhydride, but K5CoW12O40 ? 3H2O was ineffective for esterification with ethyl acetate, acetic acid, and ethyl formate.
- Rafiee,Tangestaninejad,Habibi,Mohammadpoor-Baltork,Mirkhani
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p. 393 - 395
(2007/10/03)
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- Silphos [PCl3-n(SiO2)n]: A heterogeneous phosphine reagent for formylation and acetylation of alcohols and amines with ethyl formate and acetate
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Alcohols and amines are formylated and acetylated in the presence of Silphos [PCl3-n(SiO2)n] in ethyl formate and ethyl acetate in high to excellent yields. This procedure provides a method to separate the product by a simple filtration.
- Iranpoor, Nasser,Firouzabadi, Habib,Jamalian, Arezu
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p. 7963 - 7966
(2007/10/03)
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- Acetylation and formylation of alcohols in the presence of silica sulfuric acid
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Alcohols are converted to esters in a mild, clean, and efficient reaction with acetic and formic acids in the presence of silica sulfuric acid. All reactions were performed under mild and completely heterogeneous conditions in refluxing n-hexane.
- Shirini, Farhad,Zolfigol, Mohammad Ali,Mohammadi, Kamal
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p. 1617 - 1621
(2007/10/03)
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- Bi(III) salts as new catalysts for the selective conversion of trimethylsilyl and tetrahydropyranyl ethers to their corresponding acetates and formates
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Bi(III) salts such as BiCl3, Bi(TFA)3 and Bi(OTf)3 were found to be efficient catalysts for the transformation of trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to their corresponding acetates and formates with acetic acid and ethyl formate. Selective acetylation and formylation of TMS and THP ethers of alcohols in the presence of phenolic TMS and THP ethers make this method a useful and practical procedure in organic synthesis.
- Mohammadpoor-Baltork,Khosropour
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p. 2433 - 2439
(2007/10/03)
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- Mild and highly selective formyl protection of primary hydroxyl groups
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Efficient conversion of primary alcohols to the corresponding formate esters can be carried out at room temperature in methylene chloride, using 2,4,6-trichloro-1,3,5-triazine and N,N-dimethyl- formamide in the presence of lithium fluoride. This procedure
- De Luca, Lidia,Giacomelli, Giampaolo,Porcheddu, Andrea
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p. 5152 - 5155
(2007/10/03)
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- Selective formylation of alcohols in the presence of phenols with chloral
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Primary and secondary alcohols were formylated selectively in the presence of phenols by stirring with chloral in acetone over anhydrous K2CO3 at ambient temperatures in high yields.
- Ram, Ram N,Meher, Nabin Kumar
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p. 2997 - 3001
(2007/10/03)
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- A convenient and chemoselective acetylation and formylation of alcohols and phenols using acetic acid and ethyl formate in the presence of Bi(III) salts
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A variety of alcohols are acetylated and formylated efficiently with acetic acid and ethyl formate in the presence of catalytic amounts of Bi(III) salts such as BiCl3, Bi(TFA)3 and Bi(OTf)3. BiCl3 and Bi(OTf)3 are also effective catalysts for acetylation of phenols. All of these catalysts are ineffective in formylation of phenols. Selective acetylation and formylation of alcohols in the presence of phenols is an additional advantage of this procedure.
- Mohammadpoor-Baltork,Khosropour,Aliyan
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p. 280 - 282
(2007/10/03)
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- Novel catalytic acetylation and formylation of alcohols with potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O)
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Acetylation and formylation reactions of alcohols with ethyl acetate, acetic acid and ethyl formate were catalyzed with potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O) in a mild, efficient and convenient method with high to excellent yields.
- Habibi, Mohammad H,Tangestaninejad, Shahram,Mirkhani, Valiollah,Yadollahi, Bahram
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p. 8333 - 8337
(2007/10/03)
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- Catalytic esterification of alcohols, carboxylic acids and transesterification reactions with cerium(IV) triflate
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Esterification reactions of alcohols with acetic, chloroacetic, trifluoroacetic, propionic, stearic, and benzoic acids were catalyzed with Ce(OTf)4 in a solvent or under solvent-free conditions with high yields. The formylation and acetylation of primary and secondary alcohols were also easily achieved in ethyl formate and ethyl acetate. A high retention of the configuration was observed in the acetylation and formylation of (-)-menthol.
- Iranpoor, Nasser,Shekarriz, Marzieh
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p. 455 - 458
(2007/10/03)
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- Conversion of trimethylsilyl ethers to acetyl or formyl esters with TiCl4
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A simple method is described for the efficient conversion of trimethylsilyl ethers to their corresponding acetyl and formyl esters in refluxing ethyl acetate or ethyl formate in the presence of TiCl4.
- Iranpoor, Nasser,Zeynizadeh, Behzad
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p. 2123 - 2128
(2007/10/03)
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- Selective acetylation of primary alcohols: Acetyl and formyl transfer reactions with copper(II) salts
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The efficient esterification of primary and secondary alcohols in acetic acid was achieved in the presence of Cu(NO3)2. 3H20 in high yields. Selective acetylation of primary in the presence of secondary hydroxyl groups in excellent yields were performed in EtOAc. Formylation of primary and secondary alcohols was also achieved easily in ethyl formate. High retention of configuration was observed in the acetylafion and formylation of (-) menthol in the presence of Cu(NO3)2. 3H20 and Cu(OAC)2. H2O.
- Iranpoor,Firouzabadi,Zolfigol
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p. 1923 - 1934
(2007/10/03)
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- Tf2O/Amide adducts: Versatile reagents for the synthesis of imidates and amidines
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The Vilsmeier reagents generated from tertiary and secondary aliphatic and aromatic amides and trifluoromethanesulfonic anhydride (Tf2O) reacted with different nucleophiles (ROH, RSH, RNH2) affording the relative iminium and amidinium salts. The former, stable at room temperature, were easily transformed into the corresponding esters or O-alkyl thioesters by treatment with OH- or SH-.
- Sforza, Stefano,Dossena, Arnaldo,Corradini, Roberto,Virgili, Eliana,Marchelli, Rosangela
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p. 711 - 714
(2007/10/03)
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- Convenient one-pot method for formylation of amines and alcohols using formic acid and 1,1'-oxalyldiimidazole
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1,1'-Oxalyldiimidazole (7) reacts with formic acid (8) in acetonitrile at room temperature to give N-formylimidazole (5), which promptly undergoes aminolysis and alcoholysis to yield formamides (2) or formates (4).
- Kitagawa,Arita,Nagahata
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p. 1655 - 1657
(2007/10/02)
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- FORMYLATION REACTION USING THE OZONOLYSATE OF OXAZOLE
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The ozonolysis of oxazole (1) did not give formic anhydride (3), but gave N-formylformamide (5), which reacted with various nucleophiles to afford the corresponding formylated products in high yield.This formylating reaction should be useful in the organic syntheses.
- Kashima, Choji,Arao, Hideki,Hibi, Shigeki,Omote, Yoshimori
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p. 1561 - 1562
(2007/10/02)
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- Le formamide, un substitut de l'eau dans les reactions d'echange chlore-fluor par transfert de phase solide-liquide
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The fluoride-chloride exchange reaction RCl+KF -> RF+KCl catalysed by ammonium salts, was found to take place in presence of formamide in place of water.The results, depending of RCl are discussed in this paper.
- Escoula, Brigitte,Rico, Isabelle,Lattes, Armand
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p. 256 - 259
(2007/10/02)
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- LE FORMAMIDE, UN SUBSTITUT DE L'EAU XVI 1: REACTIONS D'ECHANGE CHLORE-FLUOR EN TRANSFERT DE PHASE SOLIDE-LIQUIDE
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The chloride-fluoride exchange reaction, RCl+KF -> RF+KCl, catalised by ammonium salts, was found to take place in the presence of formamide when this is used as a replacement for water.The experimental results and their dependence on RCl are discussed in this communication.
- Escoula, B.,Rico, I.,Lattes, A.
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p. 487 - 494
(2007/10/02)
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- An Improved and Convenient Synthesis of Esters Using 1,1'-Carbonyldiimidazole and a Reactive Halide
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The esterification of carboxylic acid proceeded easily in a one-pot reaction with 1,1'-carbonyldiimidazole in the presence of a reactive halide under neutral reaction conditions in high yields. Keywords - esterification: 1,1'-carbonyldiimidazole; formylation; tert-butyl ester; imidazolium salt; one-pot reaction
- Kamijo, Tetsuhide,Harada, Hiromu,Iizuka, Kinji
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p. 5044 - 5047
(2007/10/02)
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- N,N,N',N'-TETRAMETHYLCHLOROFORMAMIDINIUM CHLORIDE AS AN EFFICIENT CONDENSATION REAGENT FOR A NOVEL ESTERIFICATION APPLICABLE TO THE MACROLIDE SYNTHESIS
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N,N,N',N'-Tetramethylchloroformamidinium chloride, prepared easily from N,N,N',N'-tetramethylurea and oxalyl chloride, is found to be an efficient condensation reagent for an esterification of carboxylic acids with alcohols umder mild conditions in one-pot procedure, and the reagent is applied to the lactonization for macrolide synthesis from ω-hydroxycarboxylic acids.
- Fujisawa, Tamotsu,Mori, Toshiki,Fukumoto, Kazumasa,Sato, Toshio
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p. 1891 - 1894
(2007/10/02)
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