- Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters
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A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.
- Nikitas, Nikolaos F.,Apostolopoulou, Mary K.,Skolia, Elpida,Tsoukaki, Anna,Kokotos, Christoforos G.
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supporting information
p. 7915 - 7922
(2021/05/03)
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- N-Aroylbenzotriazoles as Efficient Reagents for o-Aroylation in Absence of Organic Solvent
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N-Aroylbenzotriazoles have been shown to be efficient reagents for esterification in the absence of organic solvent. Grinding of N-aroylbenzoytiazoles with twofold excess of alcohols for a couple of hours at room temperature gave corresponding esters in high percentage of yields.
- Hahnvajanawong, Viwat,Phungpis, Baramee
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p. 2671 - 2674
(2021/10/25)
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- Solar and visible-light active nano Ni/g-C3N4photocatalyst for carbon monoxide (CO) and ligand-free carbonylation reactions
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In this study, we investigate the amino and alkoxycarbonylation reaction between various substituted aryl halides, benzyl iodides, and iodocyclohexane with different types of amines and alcohols in the absence of carbon monoxide gas and ligands. Similar reactions are carried out at high temperatures, in the presence of appropriate ligands, stoichiometric amounts of bases, and gaseous carbon monoxide, which endanger the health of organic chemists. We present a novel method that does not utilize ligands, bases, gaseous CO, and special conditions. This procedure is a redox reaction carried out by new economic nano Ni/g-C3N4at room temperature and under visible light. Mo(CO)6was used toin situgenerate CO, to resolve the problems caused by the use of CO gas. This protocol has the ability to be used on a gram scale by using a continuous flow reactor.
- Hosseini-Sarvari, Mona,Akrami, Zahra
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p. 956 - 969
(2021/02/26)
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- Iodine-catalyzed synthesis of β-uramino crotonic esters as well as oxidative esterification of carboxylic acids in choline chloride/urea: a desirable alternative to organic solvents
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Abstract: Iodine-mediated selective synthesis of β-uramino crotonic esters was achieved via the reaction of β-dicarbonyls and urea at room temperature. Choline chloride/urea mixture, as an eco-friendly, cheap, non-toxic, and recyclable deep eutectic solvent (DES), was employed as sustainable media as well as reagent at the same time in these transformations. Some derivatives of β-uramino crotonic esters were synthesized with good to high yields without a tedious work-up. The process could be done to synthesize the above-mentioned compounds in gram scale. Moreover, oxidative cross-esterification of carboxylic acids with alkyl benzenes was carried out in the above-mentioned DES by the employment of tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant at 80?°C. DES/TBAI system was reused up to five consecutive times. Graphic abstract: Iodine-catalyzed C–N and C–O bond formation in choline chloride/urea as a green solvent under the mild reaction conditions. Providing the clean procedure toward synthesis of β-uramino crotonic esters and benzylic esters.[Figure not available: see fulltext.].
- Moayyed, Mohammadesmaeil,Saberi, Dariush
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p. 445 - 455
(2020/09/07)
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- A metal-free iodine-mediated conversion of hydroxamates to esters
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A metal-, oxidant-, and additive-free conversion of hydroxamates to esters have been achieved using molecular iodine as the reagent using a novel but not-so-explored heron-type rearrangement. The reaction proceeds with almost equal facility with substrates having either electron-donating or electron-withdrawing substituent. Similarly, α,?-unsaturated, and sterically hindered ortho-substituted hydroxamates also undergo the desired transformation smoothly.
- Ghosh, Subhankar,Banerjee, Jeet,Ghosh, Rajat,Chattopadhyay, Shital K.
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p. 1353 - 1360
(2020/03/30)
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- Bu 4 NI-Catalyzed C-C Bond Cleavage and Oxidative Esteri??cation of Allyl Alcohols with Toluene Derivatives
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A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C-C bond cleavage and C-O bond forming.
- Chen, Yaoyao,Cui, Yongmei,Jia, Xueshun,Li, Chengliang,Li, Jian,Sun, Mingming
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p. 3667 - 3674
(2019/09/30)
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- Palladium-Catalyzed Carbonylative Synthesis of Benzyl Benzoates Employing Benzyl Formates as Both CO Surrogates and Benzyl Alcohol Sources
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An efficient and convenient palladium-catalyzed carbonylation reaction for the synthesis of benzyl benzoates from aryl bromides has been developed. Benzyl formates have been explored as a new type of efficient and useful CO sources and also reaction partners. A wide range of benzyl benzoates was obtained in good to excellent yields.
- Lai, Ming,Qi, Xinxin,Wu, Xiao-Feng
-
supporting information
p. 3776 - 3778
(2019/06/24)
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- Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required
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A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.
- Kwon, Young-Do,La, Minh Thanh,Kim, Hee-Kwon
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p. 10833 - 10841
(2018/07/05)
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- N-Methylpyrrolidin-2-one-Promoted Formation of Functional Esters through C–O Bond Cleavage
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Trifluoromethanesulfonic acid catalyzed C–O bond cleavage leading to the preparation of functional esters in the presence of N-methylpyrrolidin-2-one (NMP) was accomplished. Various substrates were well tolerated, and a gram-scale experiment was successfully realized. DFT calculations indicated that NMP plays a decisive role in accelerating nucleophilic attack of the functional acid to generate the functional esters in chlorobenzene.
- Liu, Jianming,Wang, Yanyan,Yue, Yuanyuan,Liu, Na,Zhang, Jian,Zhao, Shufang,Tang, Qinghu,Zhuo, Kelei
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supporting information
p. 2641 - 2647
(2017/05/19)
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- Oxidation-Reduction Condensation of Diazaphosphites for Carbon-Heteroatom Bond Formation Based on Mitsunobu Mechanism
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An efficient oxidation-reduction condensation reaction of diazaphosphites with various nonacidic pronucleophiles in the presence of DIAD as a weak oxidant has been developed for carbon-heteroatom bond formation. This mild process affords structurally diverse tertiary amines, secondary amines, esters, ethers, and thioethers in moderate to excellent yields. The selective synthesis of secondary amines from primary amines has been achieved. Importantly, a practical application to the synthesis of antiparkinsonian agent piribedil has been demonstrated.
- Huang, Hai,Kang, Jun Yong
-
supporting information
p. 544 - 547
(2017/02/10)
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- Polymer supported Zn-salen complexes: An effective one-pot oxidative esterification of aldehydes to carboxylic esters
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Polymer-supported Zn-salen (PS-Zn-salen) complexes were synthesized, characterized and used as a catalyst for one-pot oxidative esterification of aldehydes with alcohols. The PS-Zn-salen heterogeneous catalyst exhibited a high-performance for the oxidative esterification of aldehydes to the corresponding methyl/ethyl esters using hydrogen peroxide as a green oxidant. Due to the synergistic effect of polymer support, the heterogeneous catalyst presented superior catalytic activity and afford 100% conversion of 3,4,5-trimethoxybenzaldehyde and 4-chlorobenzaldehyde to corresponding esters under optimized conditions. The different alcohol substrates study (viz. methyl alcohol, ethyl alcohol, allyl alcohol and benzyl alcohol) showed reasonable selectivity for esters, indicating the scope of the catalysts. Significantly, the synthesized complexes possess good hydrophobic/heterogeneous properties, which permit facile reclamation of the catalyst by using mere filtration. Moreover, the effect of counter anions of complex also studied which indicated that there is no appreciable influence on the conversion of product. The catalyst was reused up to 5th successive run with the average conversion of ester 87.4%. Mechanistic studies have recognized that this “one pot” direct oxidative esterification proceeds through acid formation, proven by a GC–MS. The catalyst is also found to be very stable, up to 280?°C, confirmed by the thermo gravimetric study.
- Balinge, Kamlesh Rudreshwar,Khiratkar, Avinash Ganesh,Bhagat, Pundlik Rambhau
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p. 1085 - 1095
(2017/08/08)
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- Esterification of the Primary Benzylic C-H Bonds with Carboxylic Acids Catalyzed by Ionic Iron(III) Complexes Containing an Imidazolinium Cation
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The first iron-catalyzed esterification of the primary benzylic C-H bonds with carboxylic acids using di-tert-butyl peroxide as an oxidant is achieved by novel ionic iron(III) complexes containing an imidazolinium cation. The use of well-defined, air-stable, and available iron(III) complex in a 5 mol % loading and readily available starting materials with a broad generality and outstanding sterically hindered tolerance renders this methodology a useful alternative to other protocols that are typically employed for the synthesis of benzyl esters.
- Lu, Bing,Zhu, Fan,Sun, Hong-Mei,Shen, Qi
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supporting information
p. 1132 - 1135
(2017/03/14)
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- Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp3-H bond activation under metal-free conditions
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A metal-free protocol for the direct oxidative esterification of the Csp3-H bond in benzylic hydrocarbons with carboxylic acids using heterocyclic ionic liquid as catalyst has been reported. The catalyst 1-butylpyridinium iodide could be easily recycled and reused for at least four cycles without obvious loss of catalytic activity.
- Mou, Fen,Sun, Yadong,Jin, Weiwei,Zhang, Yonghong,Wang, Bin,Liu, Zhiqing,Guo, Lei,Huang, Jianbin,Liu, Chenjiang
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p. 23041 - 23045
(2017/07/10)
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- Mitsunobu Reaction Using Basic Amines as Pronucleophiles
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A novel protocol for extending the scope of the Mitsunobu reaction to include amine nucleophiles to form C-N bonds through the utilization of N-heterocyclic phosphine-butane (NHP-butane) has been developed. Both aliphatic alcohols and benzyl alcohols are suitable substrates for C-N bond construction. Various acidic nucleophiles such as benzoic acids, phenols, thiophenol, and secondary sulfonamide also provide the desired products of esters, ethers, thioether, and tertiary sulfonamide with 43-93% yields. Importantly, C-N bond-containing pharmaceuticals, Piribedil and Cinnarizine, have been synthesized in one step from the commercial amines under this Mitsunobu reaction system.
- Huang, Hai,Kang, Jun Yong
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p. 6604 - 6614
(2017/07/15)
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- Studies of the Electronic Effects of Zinc Cluster Catalysts and Their Application to the Transesterification of β-Keto Esters
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The electronic effects of tetranuclear zinc cluster catalysts on transesterification were investigated by changing the carboxylate ligands in the clusters. High catalyst activity crucially depended on the balance between Lewis acidity and Br?nsted basicity of the catalyst; this was consistent with the dual activation of both the electrophile and nucleophile by the cooperative zinc centers. In addition, tetranuclear zinc cluster catalysts achieved the transesterification of β-keto esters with unprecedented levels of broad substrate generality, in which a newly developed pentafluoropropionate-bridged zinc cluster and 4-dimethylaminopyridine additive greatly improved the reactivity of sterically congested α- and α,α-disubstituted β-keto esters. Lewis versus Br?nsted: High catalyst activity of zinc clusters on transesterification crucially depend on a balance between Lewis acidity and Br?nsted basicity of the catalyst. Zinc clusters, including a newly developed pentafluoropropionate-bridged zinc cluster, achieved the transesterification of β-keto esters with unprecedented levels of broad substrate generality (see figure).
- Agura, Kazushi,Hayashi, Yukiko,Wada, Mari,Nakatake, Daiki,Mashima, Kazushi,Ohshima, Takashi
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supporting information
p. 1548 - 1554
(2016/06/01)
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- NOVEL SINGLE STEP ESTERIFICATION PROCESS OF ALDEHYDES USING A HETEROGENEOUS CATALYST
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The present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using a heterogeneous catalyst with high yields. More particularly, the present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using Titanium superoxide with greater than 80% yields.
- -
-
Page/Page column 9
(2016/06/20)
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- METHOD OF CONVERTING ALCOHOL TO HALIDE
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The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.
- -
-
Page/Page column 50; 68
(2017/01/02)
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- N-Heterocyclic Carbene-Mediated Oxidative Electrosynthesis of Esters in a Microflow Cell
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An efficient N-heterocyclic carbene (NHC)-mediated oxidative esterification of aldehydes has been achieved in an undivided microfluidic electrolysis cell at ambient temperature. Productivities of up to 4.3 g h-1 in a single pass are demonstrated, with excellent yields and conversions for 19 examples presented. Notably, the oxidative acylation reactions were shown to proceed with a 1:1 stoichiometry of aldehyde and alcohol (for primary alcohols), with remarkably short residence times in the electrolysis cell (13 s), and without added electrolyte. (Chemical Equation Presented).
- Green, Robert A.,Pletcher, Derek,Leach, Stuart G.,Brown, Richard C. D.
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supporting information
p. 3290 - 3293
(2015/07/15)
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- Versatile and sustainable alcoholysis of amides by a reusable CeO 2 catalyst
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CeO2 catalyzed the esterification between an equivalent molar ratio of primary amides and alcohols under neutral conditions, which provides the first versatile reusable catalytic system for direct alcoholysis of amides to esters with wider scope and 67 times higher turnover number (TON) than previous catalytic systems.
- Siddiki, S. M. A. Hakim,Touchy, Abeda Sultana,Tamura, Masazumi,Shimizu, Ken-Ichi
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p. 35803 - 35807
(2014/11/07)
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- Electrogenerated N-heterocyclic carbene in ionic liquid: An insight into the mechanism of the oxidative esterification of aromatic aldehydes
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An N-heterocyclic carbene (NHC), generated by cathodic reduction of BMIm BF4, mediates the oxidative esterification of aromatic aldehydes with organic bromides in the corresponding ionic liquid as solvent. The product recovery by simple extractive work-up with diethyl ether allowed the ionic liquid to be recycled up to 9 times for subsequent electrolyses, with no significant loss in the product yield. The isolation of an intermediate, whose structure was confirmed by synthesis and transformation into the ester, provided the key for a mechanistic insight into the reaction.
- Forte, Gianpiero,Chiarotto, Isabella,Inesi, Achille,Loreto, Maria Antonietta,Feroci, Marta
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p. 1773 - 1781
(2014/06/09)
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- Direct, rapid and convenient synthesis of esters and thioesters using PPh3/N-chlorobenzotriazole system
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We have developed an efficient method for esterification and thioesterification of various carboxylic acids with different alcohols and thiols using PPh3/N-chlorobenzotriazole mixed reagent in CH2Cl2 at room temperature.
- Rouhi-Saadabad, Hamed,Akhlaghinia, Batool
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p. 253 - 263
(2014/02/14)
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- Transition metal free oxidative esterification of alcohols with toluene
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Using Bu4NI as the catalyst and tert-butyl hydroperoxide as the oxidant, direct esterification of alcohols with toluene derivatives was achieved. Mechanistic investigations indicate that the alcohols are sequentially oxidized to aldehydes, carboxylic acids, and then to benzyl esters. Bu 4N+ functions as a phasetransfer reagent and iodide catalyzes the reaction.
- Liu, Lianghui,Yun, Lin,Wang, Zikuan,Fu, Xuefeng,Yan, Chun-Hua
-
supporting information
p. 5383 - 5386
(2013/09/12)
-
- Aniline mediated oxidative C-C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(d)-amino acid derivatives
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A metal-free and 4-methyl aniline mediated method for the oxidative C-C bond cleavage has been developed. The reaction proceeds in air using molecular oxygen as the oxidant, affording one-carbon shortened esters in moderate to good yields within a short time. Moreover, it provides a model reaction for the highly enantioselective synthesis of (d)-serine esters by combining with a l-proline catalyzed Mannich reaction.
- Hu, Bin,Li, Yunfeng,Li, Zhongjun,Meng, Xiangbao
-
supporting information
p. 4138 - 4141
(2013/07/05)
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- NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes
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This publication describes a highly selective oxidation of aldehydes to the corresponding acids or esters. The reaction proceeds under metal-free conditions by using N-heterocyclic carbenes as organocatalysts in combination with environmentally friendly oxygen as the terminal oxidation agent.
- Moehlmann, Lennart,Ludwig, Stefan,Blechert, Siegfried
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p. 602 - 607
(2013/04/24)
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- Cooperative N-Heterocyclic Carbene (NHC) and Ruthenium Redox Catalysis: Oxidative Esterification of Aldehydes with Air as the Terminal Oxidant
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The paper describes a cooperative NHC (N-heterocyclic carbene) and ruthenium-based redox catalysis for the mild aerobic oxidative esterification of various aromatic and heteroaromatic aldehydes. The ruthenium(II) complex Ru(bpz)3(PF6)2 (bpz=2,2′-bipyrazine) as catalyst is shown to be compatible with free NHCs. The NHC is used in these cascade reactions for the umpolung of the aldehyde to form the corresponding Breslow intermediate which in turn gets oxidized to an acylazolium ion by the ruthenium redox catalyst. Air is used as a terminal oxidant for oxidation (regeneration) of the ruthenium catalyst. In addition, we will show that in the absence of the ruthenium redox catalyst and alcohol, NHC-catalyzed aerobic oxidation of aldehydes delivers the corresponding acids in good to excellent yields. Mechanistic studies and DFT calculations supporting our suggested mechanisms are provided. Copyright
- Zhao, Junfeng,Mueck-Lichtenfeld, Christian,Studer, Armido
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supporting information
p. 1098 - 1106
(2013/05/21)
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- Palladium-catalyzed benzylation of carboxylic acids with toluene via benzylic C-H activation
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Direct benzylation of carboxylic acids with toluene has been developed via palladium-catalyzed C-H acyloxylation under 1 atm of oxygen. This reaction demonstrates good functional group tolerance and high yields, providing a facile, atom-economic, and efficient method for the synthesis of benzyl esters.
- Liu, Hongqiang,Shi, Guangfa,Pan, Shulei,Jiang, Yuyu,Zhang, Yanghui
-
supporting information
p. 4098 - 4101
(2013/09/12)
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- Preparation of esters and amides from carboxylic acids and N-formylation of amines promoted by 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)
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A new method is described for the preparation of esters and amides promoted by TAPC from carboxylic acids using a solvent-free grinding technique. The solvent-free N-formylation of amines is also reported.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Targhan, Homa,Sheikh Arabi, Mehdi
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supporting information
p. 5064 - 5068
(2013/09/02)
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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
-
supporting information
p. 12570 - 12574
(2013/02/22)
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- Dimethylbut-2-ynedioate mediated esterification of acids via sp3 C-N bond cleavage of benzylic tertiary amines
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A straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acids was demonstrated in this manuscript. The present protocol can be regarded as a straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acid. Moreover, the reaction is fundamentally new chemistry for the sp 3 C-N bond cleavage coupled with esterification. The esterification reaction conditions are very mild and functional group-tolerated, such as hydrosilanes, alcohols, phenol, and amino acids. A mechanism is proposed in which the tertiary amine reacts with dimethyl but-2-ynedioate to form zwitterionic salt, and then the zwitterionic intermediate subsequently accept hydrogen to assist the nucleophilic attack of oxygen atom of carboxyl group at the benzyl group of tertiary amine, while a separate reaction pathway leads to esterification.
- Shen, Hao,Lu, Xing,Jiang, Ke-Zhi,Yang, Ke-Fang,Lu, Yixin,Zheng, Zhan-Jiang,Lai, Guo-Qiao,Xu, Li-Wen
-
supporting information
p. 8916 - 8923
(2012/10/29)
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- Copper catalyzed oxidative esterification of aldehydes with alkylbenzenes via cross dehydrogenative coupling
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Copper(II) as the catalyst in a cross dehydrogenative coupling (CDC) reaction has been demonstrated for the synthesis of benzylic esters using aldehydes and alkylbenzenes as coupling partners.
- Rout, Saroj Kumar,Guin, Srimanta,Ghara, Krishna Kanta,Banerjee, Arghya,Patel, Bhisma K.
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supporting information; experimental part
p. 3982 - 3985
(2012/09/22)
-
- Organocatalyzed anodic oxidation of aldehydes
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A method for the catalytic formation of electroauxiliaries and subsequent anodic oxidation has been developed. The process interfaces N-heterocyclic carbene-based organocatalysis with electro-organic synthesis to achieve direct oxidation of catalytically generated electroactive intermediates. We demonstrate the applicability of this method as a one-pot conversion of aldehydes to esters for a broad range of aldehyde and alcohol substrates. Furthermore, the anodic oxidation reactions are very clean, producing only H2 gas as a result of cathodic reduction.
- Finney, Eric E.,Ogawa, Kelli A.,Boydston, Andrew J.
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supporting information; experimental part
p. 12374 - 12377
(2012/09/05)
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- Tetrabutylammonium iodide catalyzed synthesis of allylic ester with tert -butyl hydroperoxide as an oxidant
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A metal-free C-H oxidation for the construction of allylic esters has been developed. The use of a commercially available and inexpensive catalyst and oxidant, and readily available starting materials, coupled with the operational simplicity of the reacti
- Shi, Erbo,Shao, Ying,Chen, Shulin,Hu, Huayou,Liu, Zhaojun,Zhang, Jie,Wan, Xiaobing
-
supporting information; experimental part
p. 3384 - 3387
(2012/08/08)
-
- NHCs-mediated benzoates formation directly from aromatic aldehydes and alkyl halides
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A NHCs-mediated benzoates formation was developed by treatment of aromatic aldehydes with alkyl halides in the presence of oxygen. Corresponding benzoate derivatives were obtained in high yields up to 99%. The reaction mechanism was also discussed and a NHCs-mediated O-alkylation and subsequent oxidation process was proposed.
- Li, Yi,Du, Wenting,Deng, Wei-Ping
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experimental part
p. 3611 - 3615
(2012/06/15)
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- Surfactant-mediated solvent-free dealkylative cleavage of ethers and esters and trans-alkylation under neutral conditions
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A simple, surfactant-mediated, one-pot, solvent-free dealkylative cleavage of aryl ethers and esters followed by subsequent optional trans-alkylation under essentially neutral conditions has been developed.
- Bhattacharya, Apurba,Patel, Nitin C.,Vasques, Tomas,Tichkule, Ritesh,Parmar, Gaurang,Wu, Jiejun
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p. 565 - 567
(2007/10/03)
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- A fast and simple method for the acylation of alcohols with acid chlorides promoted by metallic samarium
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Acylation of primary, secondary, allyl and benzyl alcohols with acid chlorides promoted by samarium metal under neutral condition gave carboxylic acid esters in good to excellent yields. Acylation of a tertiary alcohol did not occur under the same reaction conditions.
- Jia, Xue-Shun,Wang, Hai-Long,Huang, Qing,Kong, Ling-Long,Zhang, Wei-He
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p. 135 - 138
(2007/10/03)
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- Zinc promoted mild and efficient method for the esterification of acid chlorides with alcohols
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The esterification of variety of acid chlorides with alcohols in the presence of zinc is described. The easy formation of t-butyl and pivaloyl esters are the additional importance of this procedure.
- Yadav,Reddy, Gondi Sudershan,Srinivas, Dale,Himabindu, Konuru
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p. 2337 - 2342
(2007/10/03)
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- Decomposition of N,N'-Diacyl-N,N'-dialkoxyhydrazines Revisited
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N,N'-Diacyl-N,N'-dialkoxyhydrazines have been shown to decompose thermally to esters and nitrogen.An intramolecular crossover experiment has shown that the formation of esters is consistent with a three-centred rearrangement process which is characteristic of N-alkoxy N-amino amides.The four-centred mechanism previously proposed by earlier workers is less favourable energetically.AM1 molecular orbital calculations support these experimental findings.
- Buccigross, Jeanne M.,Glover, Stephen A.,Hammond, Gerard P.,Rowbottom, Colleen A.
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p. 353 - 362
(2007/10/02)
-