13756-40-6Relevant academic research and scientific papers
Reaction mechanism studies involving the correlation of the rates of solvolysis of benzoyl and p-nitrobenzoyl p-toluenesulfonates
Kevill, Dennis N.,Ryu, Zoon Ha
, p. 387 - 395 (2014)
The solvolyses of benzoyl and p-nitrobenzoyl p-toluenesulfonates (tosylates) are considerably slower than those of the previously studied mixed anhydride of acetic and p-toluenesulfonic acids (acetyl tosylate), which, even with application of rapid-response conductivity, could only be studied at considerably reduced temperatures. For the presently studied compounds, the specific rates over a wide variety of solvents could be conveniently studied at -10 °C. For solvolyses of benzoyl tosylate, application of the extended (two-term) Grunwald-Winstein equation gives sensitivities to changes in solvent nucleophilicity and solvent ionising power consistent with an ionisation (S Nl) pathway. Indeed, a good correlation is obtained against only solvent ionising power. For the solvolyses of the p-nitro-derivative, very different sensitivities are obtained, with an appreciable dependence on solvent nucleophilicity, and a dominant biomolecular pathway for the substitution is proposed for all of these solvolyses, except for those in solvents rich in fluoroalcohol. Studies of solvent deuterium isotope effects in methanolysis, of leaving-group effects relative to a halide and of temperature variation effects are consistent with the proposed mechanistic pathways.
Polyisobutylene-supported phosphines as recyclable and regenerable catalysts and reagents
Bergbreiter, David E.,Yang, Yun-Chin,Hobbs, Christopher E.
, p. 6912 - 6917 (2011)
Phosphines are important as catalysts or reagents in synthesis but must be separated from products after a reaction. This report shows that polyisobutylene (PIB)-bound alkyldiaryl- and triarylphosphines are useful as catalysts in addition and allylic amin
Vitamin B1-catalyzed aerobic oxidative esterification of aromatic aldehydes with alcohols
Chu, Xue-Qiang,Ge, Danhua,Luo, Xin-Long,Xu, Pei,Yu, Zi-Lun
supporting information, p. 30937 - 30942 (2021/11/19)
A straightforward aerobic oxidative esterification of aryl aldehydes with alcohols has been developed for the synthesis of substituted esters by employing vitamin B1 as a cost-effective, metal-free, and eco-friendly NHC catalyst. Air is used as a green terminal oxidant. The reaction is a useful addition to the existing NHC-catalytic oxidative esterification.
Br?nsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C?N Bond Cleavage; One-Step Synthesis of 2-Substituted Benzothiazoles
Biswas, Srijit,Biswas, Subrata,Duari, Surajit,Elsharif, Asma M.,Maity, Srabani,Roy, Arnab
supporting information, p. 3569 - 3572 (2021/07/22)
We have developed a Br?nsted acid mediated synthetic method to directly cleave stable amide C?N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2-substituted benzothiazole derivatives have been synthesized in one pot employing 2-aminothiophenol as nucleophile.
Solar and visible-light active nano Ni/g-C3N4photocatalyst for carbon monoxide (CO) and ligand-free carbonylation reactions
Hosseini-Sarvari, Mona,Akrami, Zahra
, p. 956 - 969 (2021/02/26)
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.
Nickel-Catalyzed Esterification of Amides Under Mild Conditions
Li, Jun-Fei,Wang, Yao-Fang,Wu, Yuan-Yuan,Liu, Wen-Jing,Wang, Jun-Wen
, p. 874 - 880 (2019/11/13)
Abstract: The use of ligands to adjust the catalytic activity of the catalyst for esterification of amides is challenge in organic chemistry. In this paper, Nickel(II)-NHC-catalyzed the esterification reaction between N,N-di-Boc amide and alcohols at room temperature have been demonstrated. The imidazolium salt bearing a hydroxyl functionalized side arm showed high effective catalytic activity in the activation of the amide N–C bond in air atmosphere. Graphic Abstract: [Figure not available: see fulltext.].
Carbon monoxide is used as a source of halogen compound heterogeneous palladium catalyst in the presence of the aldehyde carbonyl compound by reaction carbonylation method (by machine translation)
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Paragraph 0067; 0078; 0079; 0080, (2018/04/06)
[Problem] catalyst and the presence of carbon monoxide, the halogen compound is a carbonyl compound in the carbonylation reaction, catalysts or carbon monoxide source technique has problems. [Solution] the presence of the catalyst and the carbon monoxide, the halogen compound is carbonylation reaction method for producing a carbonyl compound, As a heterogeneous palladium catalyst, carbon monoxide is produced from an aldehyde carbonyl compound used in the method. [Drawing] no (by machine translation)
Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols
Chen, Zhengwang,Wen, Yuelu,Fu, Yejuan,Chen, Hai,Ye, Min,Luo, Guotian
supporting information, p. 981 - 985 (2017/05/05)
Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloro-ethane solvent with good catalytic activity.
Heterogeneous One-Pot Carbonylation and Mizoroki–Heck Reaction in a Parallel Manner Following the Cleavage of Cinnamaldehyde Derivatives
Hattori, Tomohiro,Ueda, Shun,Takakura, Ryoya,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
, p. 8196 - 8202 (2017/06/23)
Carbon monoxide (CO) and styrene derivatives that can be both generated by a palladium on carbon (Pd/C)-catalyzed carbon–carbon (C?C) bond cleavage reaction of cinnamaldehyde derivatives were effectively utilized in further palladium-catalyzed C?C bond forming reactions in a direct and practical way. CO derived from simple and affordable CO carriers such as cinnamaldehyde or terephthalaldehyde was efficiently employed in the in situ CO fixation with various aromatic iodides through a palladium-catalyzed carbonylation followed by an inter- or intramolecular coupling reaction with alcohols to afford the corresponding esters or lactones, respectively. Styrene derivatives were also efficient substrates in an in situ Mizoroki–Heck-type cross-coupling reaction with aryl iodides, leading to the effective formation of asymmetric stilbenes. The decarbonylation of cinnamaldehyde derivatives and the subsequent independent syntheses of both esters/lactones and 1,2-diarylethenes could be achieved in a virtual one-pot and in situ reaction using a H-shaped pressure-tight glass-sealed tube consisting of two independent but laterally connected reaction tubes in the gas space.
The use of BrCCl3-PPh3 in Appel type transformations to esters, O-acyloximes, amides, and acid anhydrides
Al-Azani, Mariam,al-Sulaibi, Mazen,al Soom, Nuha,Al Jasem, Yosef,Bugenhagen, Bernhard,Al Hindawi, Bassam,Thiemann, Thies
, p. 921 - 932 (2016/08/08)
Esters, acyloximes, amides and acid anhydrides have been prepared from the respective carboxylic acids, oximes, amines and alcohols by the use of the reagent combination BrCCl3-PPh3. The reactions obviate the handling acyl halides or more aggressive reagents PCl3, POCl3, or SOCl2. Furthermore, the environmentally hazardous CCl4 used in Appel-type reactions is replaced with BrCCl3, a reagent of less environmental concern.
