- Zinc-catalyzed depolymerization of artificial polyethers
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Recycling polymers: In the present study, the efficient zinc-catalyzed depolymerization of a variety of artificial polyethers has been investigated. Chloroesters were obtained as the depolymerization products, which are suitable precursors for new polymer
- Enthaler, Stephan,Weidauer, Maik
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Read Online
- IrIII-Catalyzed direct syntheses of amides and esters using nitriles as acid equivalents: A photochemical pathway
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An unprecedented IrIII[df(CF3)ppy]2(dtbbpy)PF6-catalyzed simple photochemical process for direct addition of amines and alcohols to the relatively less reactive nitrile triple bond is described herein. Various amides and esters are synthesized as the reaction products, with nitriles being the acid equivalents. A mini-library of different types of amides and esters is made using this mild and efficient process, which uses only 1 mol% of photocatalyst under visible light irradiation (λ = 445 nm). The reaction strategy is also efficient for gram-scale synthesis.
- Talukdar, Ranadeep
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supporting information
p. 5303 - 5308
(2020/04/17)
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- A Straightforward Conversion of Activated Amides and Haloalkanes into Esters under Transition-Metal-Free Cs 2 CO 3 /DMAP Conditions
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The esterification of activated amides, N -acylsaccharins, under transition-metal-free conditions with good functional group tolerance has been developed, resulting in C-N cleavage leading to efficient synthesis of a variety of esters in moderate to good yields. This work demonstrates that esterification may proceed by using simple N -acylsaccharins, haloalkanes, and Cs 2 CO 3 as oxygen source.
- Chen, Liuqing,Gu, Ying,Jian, Junsheng,Liu, Yueping,Miao, Liqiong,Wang, Zijia,Zeng, Zhuo
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p. 4078 - 4084
(2019/10/28)
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- Synthesis of Esters from Stable and Convenient Sulfoxonium Precursors under Catalyst- And Additive-Free Conditions
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A convenient and efficient procedure for the construction of esters from stable sulfoxonium ylides and alcohols has been developed. This protocol presents a broad substrate scope and good yields of the desired esters can be isolated. Notably, no catalyst, oxidant, base or any other additive is required.
- Wu, Xiao-Feng,Yuan, Yang
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supporting information
p. 1820 - 1824
(2019/09/09)
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- A Three-Phase Four-Component Coupling Reaction: Selective Synthesis of o-Chloro Benzoates by KCl, Arynes, CO2, and Chloroalkanes
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A transition-metal-free three-phase four-component coupling reaction (3P-4CR) involving KCl, arynes, chloroalkanes and CO2 has been reported for the first time, enabling the incorporation of both chloro and CO2 into an aryne simultaneously. The reactions for the synthesis of different types of o-chloro benzoates can be selectively modulated by the chloroalkane utilized. The corresponding products can be alternatively transformed for postsynthetic functionalizations conveniently.
- Jiang, Huanfeng,Zhang, Yu,Xiong, Wenfang,Cen, Jinghe,Wang, Lu,Cheng, Ruixiang,Qi, Chaorong,Wu, Wanqing
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supporting information
p. 345 - 349
(2019/01/24)
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- Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas
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A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.
- Pandey, Ganesh,Koley, Suvajit,Talukdar, Ranadeep,Sahani, Pramod Kumar
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supporting information
p. 5861 - 5865
(2018/09/21)
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- Method for generating ester through reaction of acyl chloride and 1,2-dichloroethane
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The invention discloses a method for generating ester through reaction of acyl chloride and 1,2-dichloroethane. The method comprises the following steps: taking acyl chloride, 1,2-dichloroethane and carbonate as reaction substrates, and taking 4-dimethyla
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Paragraph 0021; 0022; 0023; 0024
(2017/08/30)
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- Synthesis and Characterization of Fatty Acid Conjugates of Niacin and Salicylic Acid
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This report describes the synthesis and preliminary biological characterization of novel fatty acid niacin conjugates and fatty acid salicylate conjugates. These molecular entities were created by covalently linking two bioactive molecules, either niacin
- Vu, Chi B.,Bemis, Jean E.,Benson, Ericka,Bista, Pradeep,Carney, David,Fahrner, Richard,Lee, Diana,Liu, Feng,Lonkar, Pallavi,Milne, Jill C.,Nichols, Andrew J.,Picarella, Dominic,Shoelson, Adam,Smith, Jesse,Ting, Amal,Wensley, Allison,Yeager, Maisy,Zimmer, Michael,Jirousek, Michael R.
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supporting information
p. 1217 - 1231
(2016/02/23)
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- An Effective Method for the Construction of Esters Using Cs2CO3 as Oxygen Source
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An effective method for the construction of esters from acyl chloride and halohydrocarbon using Cs2CO3 as an oxygen source was achieved for the first time. The methodology has a wide scope of substrates and can be scaled up. The study of a preliminary reaction mechanism demonstrated that the O in the products comes from Cs2CO3 and this esterification proceeds through a free radical reaction. It was also found that CO2 can also be used in this esterification reaction as an oxygen source.
- Ren, Lanhui,Wang, Lianyue,Lv, Ying,Li, Guosong,Gao, Shuang
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p. 5172 - 5175
(2015/11/24)
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- Synthesis of piperazine derivatives and biological evaluation of its inhibitory activities on vascular smooth muscle cell proliferation
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A series of new N-substituted benzyl piperazine derivatives were synthesized using the appropriate synthetic route. The new compounds were characterized by IR, 1H NMR, MS and elemental analysis. All the compounds were screened for their inhibitory activities on vascular smooth muscle cell proliferation. Some of the compounds demonstrated moderate to good inhibition of vascular smooth muscle cell proliferation. The compounds (2h, 6h) were approximately equivalent in activity to heparin as a potent inhibitor. The possible structure-activity relationship of the inhibitory activity of all compounds was also discussed.
- Han, Sheng Hua,Chen, Jian Xin,Liu, Hong Yan,Zhang, Hai Rong,Ma, Peng Fei
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p. 1299 - 1303
(2015/02/19)
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- Copper-catalyzed Csp3-O cross-coupling of unactivated alkyl halides with organic peroxides
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An efficient Cu-catalyzed Csp3-O coupling of peroxides with haloalkanes is described. High yields of products were achieved under mild conditions. Significantly, in addition to primary alkyl halides, secondary alkyl halogenated hydrocarbons could also be applied to this system. The new reaction system could tolerate a wide range of organic peroxides.
- Chen, Huan-Huan,Wang, Guang-Zu,Han, Jin,Xu, Meng-Yu,Zhao, Yong-Qiang,Xu, Hua-Jian
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p. 212 - 217
(2014/01/06)
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- Synthesis of acyloxyalkyl esters of thiocarbonic and dithiocarbamic acids
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Reactions of acyloxyalkyl chloride with alkaline salts of alkylxanthic, butyltrithiocarbonic, and diethyldithiocarbamic acids afforded a series of acyloxyalkyl esters of various nature and positions of the acyl groups in the molecule.
- Mustafaev,Kulieva,Mustafaev,Kulibekova,Kakhramanova,Safarova,Novotorzhina
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p. 198 - 203
(2013/07/25)
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- Synthesis of esters from aldehydes or carboxylic acids with dichloromethane, dichloroethane or dichloropropane under mild conditions
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Dichloromethane (DCM) as a C1 source has been discovered: methylene diesters from DCM and carboxylic acids or aldehydes with TBHP in water were efficiently synthesized. The reactions proceed under mild conditions and afford both aliphatic and aromatic met
- Lin, Feng,Feng, Qiang,Cui, Xiuling,Song, Qiuling
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p. 20246 - 20253
(2013/11/06)
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- Transition-metal-free aerobic oxidative cleavage of C-C bonds in α-hydroxy ketones and mechanistic insight to the reaction pathway
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Clear cut: For the title reaction, O2, the ideal oxidant, was used as the only oxidizing reagent. The dimer intermediate (see scheme) and isotopic labeling control experiments with 18O2 partially disclosed the reaction mec
- Liu, Hui,Dong, Chao,Zhang, Zeguang,Wu, Peiyu,Jiang, Xuefeng
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supporting information
p. 12570 - 12574
(2013/02/22)
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- Organocatalytic selective benzoylation of alcohols with trichloromethyl phenyl ketone: Inverse selectivity in benzoylation of alcohols containing phenol or aromatic amine functionality
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Trichloromethyl phenyl ketone benzoylates primary and secondary aliphatic alcoholic groups in compounds also containing a phenolic group in the presence of 2-10 mol % of PMDETA organocatalyst at room temperature in high yields and excellent selectivity. It also shows the potential to selectively benzoylate primary alcoholic groups of aminoarylalkanols and primary-secondary diols as well as primary amino group of alkyl amines in the presence of aryl amines under similar conditions. A rationale for the selectivity and efficiency of the reaction has been provided.
- Ram, Ram N.,Soni, Vineet Kumar,Gupta, Dharmendra Kumar
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p. 9068 - 9075
(2012/11/07)
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- Low-temperature iron-catalyzed depolymerization of polyethers
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Iron will: The iron-catalyzed depolymerization of a range of polyethers is studied. The products of the depolymerization reactions are chloroesters, which can be used as starting materials for new polymers. In the presence of simple iron salts extraordinary catalyst activities and selectivities are feasible at low temperature. Copyright
- Enthaler, Stephan,Weidauer, Maik
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scheme or table
p. 1195 - 1198
(2012/08/28)
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- Total synthesis of enigmazole a from cinachyrella enigmatica. Bidirectional bond constructions with an ambident 2,4-disubstituted oxazole synthon
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The first total synthesis of the cytotoxic marine macrolide enigmazole A has been completed in 22 steps (longest linear sequence). The sensitive, densely functionalized 2,4-disubstituted oxazole fragment was constructed using an efficient Negishi-type cou
- Skepper, Colin K.,Quach, Tim,Molinski, Tadeusz F.
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supporting information; experimental part
p. 10286 - 10292
(2010/09/06)
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- Triphenylphosphine dibromide: a simple one-pot esterification reagent
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We report a one-pot, expedient protocol for the conversion of carboxylic acids to their esters using excess triphenylphosphine dibromide, base, and the alcohol. The reaction gave the esterified product in moderate-to-high yields (30-95%). For chiral acids, the reaction proceeded with little or no racemization. Use of a chiral alcohol in this transformation gave the ester with retention of configuration of the stereogenic center. Information is presented indicating that esterification proceeds through the intermediate generation of an acyloxyalkoxyphosphorane and where steric interactions play an important role in the energetics of the reaction.
- Salomé, Christophe,Kohn, Harold
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supporting information; experimental part
p. 456 - 460
(2009/04/06)
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- Oxidative transformation of 1,3-dioxacycloalkanes induced by chlorine dioxide
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The products and kinetic regularities of the reactions of 1,3-dioxacycloalkanes with chlorine dioxide were studied. The effects of the nature of solvent and the temperature on the reaction rate were considered and the activation parameters were determined.
- Abdrakhmanova,Kabal'nova,Rol'nik,Yagafarova,Shereshovets
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p. 1755 - 1760
(2007/10/03)
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- Group 5 and group 6 metal halides as very efficient catalysts for acylative cleavage of ethers
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Group 5 and 6 metal chlorides such as MoCl5, WCl6, NbCl5 and TaCl5 were found as very efficient catalysts for acylative cleavage of the C-O bond of ethers. Compared with conventional Lewis acid catalysts such as ZnCl2, AlCl3, SnCl4 and TiCl4, group 5 and 6 metal chlorides showed better results in the catalytic C-O bond cleavage of dibutyl ether with benzoyl chloride.
- Guo, Qiaoxia,Miyaji, Taichi,Hara, Ryuichiro,Shen, Baojian,Takahashi, Tamotsu
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p. 7327 - 7334
(2007/10/03)
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- N-substituted azabicycloheptane derivatives, their preparation and use
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Compounds of the formula I STR1 where the substituents have the meanings given in the description, and their preparation are described. The novel compounds are suitable for the control of diseases.
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- A new synthetic method for haloalkyl carboxylic esters from the radical ring cleavage of cyclic acetals with haloform
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A one-pot reaction of cyclic acetals with haloform catalyzed by AIBN(2,2'-azobisisobutyronitrile) provides a novel convenient way to prepare directly haloalkyl carboxylic esters in good yields.
- Hai-Xia, Lin,Liang-Heng, Xu,Nai-Ju, Huang
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p. 303 - 306
(2007/10/03)
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- Palladium(II)-mediated oxidation of alcohols using 1,2-dichloroethane as Pd(0) reoxidant
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The oxidation of primary and secondary, saturated, allylic or benzylic, alcohols is carried out in 1,2-dichloroethane at reflux using catalytic amounts of both PdCl2 and Adogen 464 in the presence of an excess of sodium carbonate. High selectivities are obtained from saturated and benzylic, secondary alcohols. Primary alcohols afford mixtures of aldehydes and esters. The migration of the double bond of α,β-unsaturated alcohols is a competing reaction. It is clearly shown that 1,2-dichloroethane reoxidizes the Pd(0) species.
- Ait-Mohand,Henin,Muzart
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p. 2473 - 2476
(2007/10/02)
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- Aromatic Nitration under Neutral Conditions Using Nitrogen Dioxide and Ozone as the Nitrating Agent. Application to Aromatic Acetals and Acylal
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Cyclic acetals derived from aromatic carbonyl compounds can be nitrated smoothly with nitrogen dioxide in ice-cooled dichloromethane or acetonitrile in the presence of ozone and magnesium oxide to give ortho- and para-nitro derivatives as the major product in good combined yields, the acetal ring as a protective group remaining almost intact.An acylal derived from benzaldehyde similarly undergoes nitration on the aromatic ring to give an isomeric mixture of three nitro compounds, in which the ortho and meta isomers predominate, while aromatic orthoesters are rapidly decomposed to give simply the parent esters.Ring nitration under neutral conditions has been interpreted in terms of a nonclassical mechanism, in which nitrogen trioxide is involved as the initial electrophile.
- Suzuki, Hitomi,Yonezawa, Shuji,Mori, Tadashi
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p. 1535 - 1544
(2007/10/03)
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- Pyridinium dichromate-assisted oxidative cleavage of α-functionalized benzylic alcohols by sodium percarbonate under phase-transfer conditions
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The course and the efficacy of the oxidation by sodium percarbonate of benzylic alcohols, α-substituted by a keto, hydroxy, ester or acid group, are dependent on the nature of both α-group and the solvent, and yields are usually improved by the presence of catalytic amounts of Cr(VI) species. The oxidative cleavage of the C(OH)-C(α) bond is the main process observed.
- Mohand,Levina,Muzart
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p. 2051 - 2059
(2007/10/02)
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- Reactions of 1,3-dioxolanes with Iodine Monochloride: Formation of Chlorohydrin Esters and Diol Monoesters
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2-Mono-substituted 1,3-dioxolanes are oxidised by iodine monochloride to the appropriate 2-substituted 1,3-dioxolan-2-ylium ions, whose stability is dependent upon the presence and nature of substituents on C-4 and C-5.Some dioxolanylium ions are labile and under the reaction conditions afford chlorohydrin esters, with inversion of configuration taking place at the ring carbon attacked by chloride.Others are stable under the reaction conditions and may be converted on aqueous workup to diol monoesters with retention of configuration at C-4 and C-5.The effect of substituents and reaction conditions on these competing reactions are described.The stereo- and regio-chemistry of both hydroxy- and chloro-ester formation was confirmed through NMR studies, which necessitated the prior detailed analysis of the 1H and 13C spectra associated with the acyloxy sidechains of the relevant esters.
- Glass, Beverley D.,Goosen, Andre,McCleland, Cedric W.
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p. 2175 - 2182
(2007/10/02)
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- Process for making esters
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Carboxylic acid esters are produced by the reaction of a carboxylic acid halide with a carbonate ester in the presence of an initiator. The reaction of a dicarboxylic acid dihalide and a bis(alkyl carbonate) ester produces a polymeric polyester.
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- Reaction of 1,3-dioxolans with Iodine Monochloride: the Scope and Mechanism of Formation of 1,3-dioxolan-2-ylium Dichloroiodates(I)
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Treatment of a series of 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolanes with iodine monochloride afforded the appropriate 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolan-2-ylium dichloroiodate(I) salts in excellent yields.In contrast to the stable 2-aryl-substituted salts, the 2-alkyl and unsubstituted derivatives were relatively labile.While 2-phenyl-1,3-dioxolan and 2-phenyl-1,3-dioxan afforded low yields of unstable salts,crystalline products could not be isolated from 4,5-disubstituted dioxolans.The reaction was inhibited by electron-withdrawing 4- and 5-substituents.From a study of the effects of photolysis and added iodine, the mechanism is proposed to involve a hydride ion transfer.Possible reasons for the formation of dichloroiodate(I) rather then monohalide salts, are outlined.The stability of the 2-aryl-substituted salts is dicussed in terms of charge distribution in the cation and possible aryl-anion interactions.
- Goosen, Andre,McCleland, Cedric W.
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p. 977 - 983
(2007/10/02)
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