1523-11-1Relevant articles and documents
Synthesis of novel N- and S-derivatives of 2-naphthol – Promising ligands for the binuclear copper complexes
Abdullin, Marat F.,Akhmadiev, Nail S.,Akhmetova, Vnira R.,Bikbulatova, El'mira M.,Ibragimov, Askhat G.,Mescheryakova, Ekaterina S.
, (2020)
N- And S-ligands for binuclear copper complexes were synthesized by the C-sp2-aminomethylation of 2-naphthol with N,N,N′,N′-tetramethyldiaminomethane giving 1-dimethylaminomethyl-2-naphthol, which then reacted with 1,2-ethanedithiol to be converted to thiomethylated derivative. Direct thiomethylation of 2-naphthol and its acetate with formaldehyde and 1,2-ethanedithiol is nonselective, because the reaction involves both O- and C-sp2 reaction centers of the substrate. Binuclear copper complexes with Cu-O-Cu-N or Cu-Cl-Cu-S bonds were prepared.
Influence of N-Cetyl-N,N,N-Trimethylammonium Bromide Counterions in the Basic Hydrolysis of Negatively Charged Aromatic Esters
Vera, S.,Rodenas, E.
, p. 3414 - 3417 (1986)
The addition of counterions, Br-, in the basic hydrolysis of some negatively charged aromatic esters in cationic micelles of N-cetyl-N,N,N-trimethylammonium bromide displaces the substraces from the micellar phase to the aqueous phase.This effect is related to the different interactions of esters with the micelle.
New microporous lanthanide organic frameworks. synthesis, structure, luminescence, sorption, and catalytic acylation of 2-Naphthol
Bahrin, Lucian Gabriel,Bejan, Dana,Janiak, Christoph,K?kcam-Demir, ülkü,Lozan, Vasile,Marangoci, Narcisa Laura,Shova, Sergiu
, (2020)
New metal-organic frameworks (MOF) with lanthanum(III), cerium(III), neodymium(III), europium(III), gadolinium(III), dysprosium(III), and holmium(III)] and the ligand precursor 1,3,5-tris(4-carboxyphenyl)-2,4,6-trimethylbenzene (H3L) were synthesized unde
INHIBITON EFFECT OF CATIONIC MICELLES ON THE BASIC HYDROLYSIS OF AROMATIC ESTERS
Vera, S.,Rodenas, E.
, p. 143 - 150 (1986)
The basic hydrolysis of 4-acetoxybenzoic acid and 2-naphtylacetate have been studied in cationic micelles of N-cetyl-N,N,N-trimethylammonium bromide and hydroxide and the results compared with the ones obtained for the basic hydrolysis of acetylsalicylic acid and 3-acetoxy2-naphtoic acid.The results can be explained with the pseudophase kinetic model and the determined second order rate constants in micelles are also smaller than the second order rate constants in water.
Noncross-linked polystyrene nanoencapsulation of ferric chloride: A novel and reusable heterogeneous macromolecular Lewis acid catalyst toward selective acetylation of alcohols, phenols, amines, and thiols
Alinejad, Sara,Donyapeyma, Ghazaleh,Rahmatpour, Ali
, (2022/01/24)
Ferric chloride has been successfully nanoencapsulated for the first time on a non-cross-linked polystyrene matrix as the shell material via the coacervation technique. The resulting polystyrene nanoencapsulated ferric chloride was used as a novel and rec
Method for promoting acylation of amine or alcohol by carbon dioxide
-
Paragraph 0034-0035, (2021/05/29)
The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.
Magnetically recyclable silica-coated ferrite magnetite-K10montmorillonite nanocatalyst and its applications in O, N, and S-acylation reaction under solvent-free conditions
Kumar, Pushpendra,Patil, Shripad M.,Tandon, Nitin,Tandon, Runjhun
, p. 21291 - 21300 (2021/07/01)
Novel silica-coated ferrite nanoparticles supported with montmorillonite (K10) have been prepared successfully by using a simple impregnation method. Further, these nanoparticles were characterized by using different analytical methods like FT-IR, PXRD, EDS, and FE-SEM techniques. In addition, these nanoparticles have been explored for their catalytic activity for the O, N, and S-acylation reactions under solvent-free conditions which gave moderate to excellent yields in a much shorter reaction time. Moreover, these nanoparticles could easily be separated out from the reaction medium after the reaction completion by using an external magnetic field and have been re-used for 10 cycles without any significant loss of the catalytic activity.
Steric effect of NHC ligands in Pd(II)–NHC-catalyzed non-directed C–H acetoxylation of simple arenes
Mandal, Tanmoy,Yadav, Sudha,Choudhury, Joyanta
, (2021/09/06)
Although there has been a lot of progress in oxidative arene C–H functionalization reactions catalyzed by Pd(II/IV) system, the non-directed, site-selective functionalization of arene molecules is still challenging. It has been established that ligands play a pivotal role in controlling rate- as well as selectivity-determining step in a catalytic cycle involving well-defined metal-ligand bonding. N-heterocyclic carbene (NHC) ligands have had a tremendous contribution in the recent extraordinary success of achieving high reactivity and excellent selectivity in many catalytic processes including cross-coupling and olefin-metathesis reactions. However, the immense potential of these NHC ligands in improving site-selectivity of non-directed catalytic C–H functionalization reactions of simple arenes is yet to be realized, where overriding the electronic bias on deciding selectivity is a burdensome task. The presented work demonstrated an initiative step in this regard. Herein, a series of well-defined discrete [Pd(NHCR′R)(py)I2] complexes with systematically varied degree of spatial congestion at the Pd centre, exerted through the R and R’ substituents on the NHC ligand, were explored in controlling the activity as well as the site-selectivity of non-directed acetoxylation of representative monosubstituted and disubstituted simple arenes (such as toluene, iodobenzene and bromobenzene, naphthalene and 1,2-dichlorobenzene). The resulting best yields were found to be 75% for toluene and 65% for bromobenzene with [Pd(NHCMePh)(py)I2], 75% for iodobenzene and 79% for naphthalene with [Pd(NHCMeMe)(py)I2], and 41% for 1,2-dichlorobenzene with [Pd(NHCCyCy)(py)I2]. Most importantly, with increasing the bulkiness of the NHC ligand in the complexes, the selectivity of the distal C-acetoxylated products in comparison to the proximal ones, was enhanced to a great extent in all cases. Considering the vast library of NHC ligands, this study underscores the future opportunity to develop more strategies to improve the activity and the crucial site-selectivity of C–H functionalization reactions in simple as well as complex organic molecules.
Nickel-Mediated Trifluoromethylation of Phenol Derivatives by Aryl C?O Bond Activation
Hu, Wei-Qiang,Pan, Shen,Qing, Feng-Ling,Vicic, David A.,Xu, Xiu-Hua
supporting information, p. 16076 - 16082 (2020/07/04)
The increasing pharmaceutical importance of trifluoromethylarenes has stimulated the development of more efficient trifluoromethylation reactions. Tremendous efforts have focused on copper- and palladium-mediated/catalyzed trifluoromethylation of aryl halides. In contrast, no general method exists for the conversion of widely available inert electrophiles, such as phenol derivatives, into the corresponding trifluoromethylated arenes. Reported herein is a practical nickel-mediated trifluoromethylation of phenol derivatives with readily available trimethyl(trifluoromethyl)silane (TMSCF3). The strategy relies on PMe3-promoted oxidative addition and transmetalation, and CCl3CN-induced reductive elimination. The broad utility of this transformation has been demonstrated through the direct incorporation of trifluoromethyl into aromatic and heteroaromatic systems, including biorelevant compounds.
KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot
Gurawa, Aakanksha,Kumar, Manoj,Rao, Dodla S.,Kashyap, Sudhir
supporting information, p. 16702 - 16707 (2020/10/27)
A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is
