16737-30-7Relevant academic research and scientific papers
Ultra-high surface area functional porous polymers by emulsion templating and hypercrosslinking: Efficient nucleophilic catalyst supports
Pulko, Irena,Wall, Jennifer,Krajnc, Peter,Cameron, Neil R.
, p. 2350 - 2354 (2010)
The action is at the surface: Ultra-high surface area emulsion templated porous polymers are prepared by the hypercrosslinking method. Control of the extent of conversion of benzyl chloride groups leaves residual accessible functionality for subsequent im
Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives
Hayashi, Hiroyuki,Yasukochi, Shotaro,Sakamoto, Tatsuhiro,Hatano, Manabu,Ishihara, Kazuaki
, p. 5197 - 5212 (2021/04/12)
Insight into the mechanism of a safe, simple, and inexpensive phosphoric acid (H3PO4)-catalyzed acylation of alcohols with acid anhydrides is described. The corresponding in situ-generated diacylated mixed anhydrides, unlike traditionally proposed monoacylated mixed anhydrides, are proposed as the active species. In particular, the diacylated mixed anhydrides act as efficient catalytic acyl transfer reagents rather than as Br?nsted acid catalysts simply activating acid anhydrides. Remarkably, highly efficient phosphoric acid (1-3 mol %)-catalyzed acylation of alcohols with acid anhydrides was achieved and a 23 g scale synthesis of an ester was demonstrated. Also, phosphoric acid catalyst was effective for synthetically useful esterification from carboxylic acids, alcohols, and acid anhydride. Moreover, with regard to recent developments in chiral 1,1′-bi-2-naphthol (BINOL)-derived phosphoric acid diester catalysts toward asymmetric kinetic resolution of alcohols by acylation, some phosphate diesters were examined. As a result, a 31P NMR study and a kinetics study strongly supported not only the acid-base cooperative mechanism as previously proposed by other researchers but also the mixed anhydride mechanism as presently proposed by us.
Isopropenyl acetate: A cheap and general acylating agent of alcohols under metal-free conditions
Temperini, Andrea,Minuti, Lucio,Morini, Tommaso,Rosati, Ornelio,Piazzolla, Francesca
, p. 4051 - 4053 (2017/09/27)
Functionalized primary, secondary and tertiary alcohols are efficiently acetylated by isopropenyl acetate and catalytic p-TsOH.
Lewis basic ionic liquid as an efficient and facile catalyst for acetylation of alcohols, phenols, and amines under solvent-free conditions
Ji, Li,Qian, Chao,Chen, Xin-Zhi
, p. 369 - 374 (2013/05/21)
The Lewis basic ionic liquid 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate was employed for the acetylation of various phenols, alcohols, and amines in good-to-excellent yields at 50 C under solvent-free conditions in a short time. Compared with existing methods based on conventional catalysts and toxic solvents, the reported method is simple, mild and environmentally viable. Furthermore, the ionic liquid was conveniently separated from the products and easily recycled to catalyze other acetylation reactions with excellent yields. .
Iron(III) tosylate catalyzed acylation of alcohols, phenols, and aldehydes
Baldwin, Neil J.,Nord, Anna N.,O'Donnell, Brendan D.,Mohan, Ram S.
, p. 6946 - 6949 (2013/01/15)
Iron(III) p-toluenesulfonate (tosylate) is an efficient catalyst for acetylation of alcohols, phenols, and aldehydes. The acetylation of 1° and 2° alcohols, diols, and phenols proceeded smoothly with 2.0 mol % of catalyst. However, the reaction worked well with only a few 3° alcohols. The methodology was also applicable to the synthesis of a few benzoate esters but required the use of 5.0 mol % catalyst. Aldehydes could also be converted into the corresponding 1,1-diesters (acylals) under the reaction conditions. Iron(III) tosylate is an inexpensive, and easy to handle, commercially available catalyst.
Simple and efficient method for acetylation of alcohols, phenols, amines, and thiols using anhydrous NiCl2 under solvent-free conditions
Meshram, Gangadhar,Patil, Vishvanath D.
experimental part, p. 4384 - 4395 (2010/04/29)
Solvent-free acetylation of alcohols, phenols, amines, and thiols with acetic anhydride (Ac2O) in the presence of 0.1mol% (13mg) anhydrous NiCl2, an inexpensive and easily available catalyst, is described. Excellent yields, short reaction time, and mild reaction conditions are important features of this method.
Development of more potent 4-dimethylaminopyridine analogues
Singh, Satwinder,Das, Goutam,Singh, Om V.,Han, Hyunsoo
, p. 401 - 404 (2008/02/12)
The syntheses of bicyclic diaminopyridines 3 and 4 and tricyclic triaminopyridines 5 and 6, two novel series of nucleophilic catalysts, are described. Arguments are made for predicting the superiority of these catalysts over DMAP and even 2, the best esterification catalyst reported to date. The efficiencies of DMAP, PPY, and 2-6 in catalyzing the esterification of tertiary alcohols were compared. As predicted, 5 and 6 were about 6-fold more effective than DMAP and slightly better than 2.
A novel 3-nitrobenzeneboronic acid as an extremely mild and environmentally benign catalyst for the acetylation of alcohols under solvent-free conditions
Tale,Adude
, p. 7263 - 7265 (2007/10/03)
A novel 3-nitrobenzeneboronic acid is found to catalyse efficiently the acetylation of a wide range of alcohols as well as phenols with acetic anhydride in good to excellent yields at room temperature under solvent-free conditions. The reactions are clean and the catalyst is mild such that highly sensitive functional groups including oximes are stable to the reaction conditions.
A mild and efficient method for the acetylation of alcohols
Shirini,Zolfigol,Safari
, p. 201 - 203 (2007/10/03)
The acetylatioh of alcohols has been carried out efficiently in the presence of a catalytic amount of Zr(HSO4)4. All reactions are performed at room temperature and under heterogeneous conditions in good to high yields.
Effects of polymer architecture and nanoenvironment in acylation reactions employing dendritic (Dialkylamino)pyridine catalysts
Helms, Brett,Liang, Catherine O.,Hawker, Craig J.,Frechet, Jean M. J.
, p. 5411 - 5415 (2008/02/01)
The role of architecture and nanoenvironment in the catalytic properties of dendritic polymers containing 4-(dialkylamino)pyridines was investigated in the context of acylation reactions employing sterically demanding tertiary alcohols as substrates. Frechet-type benzyl ether and aliphatic ester dendrimers were prepared in a convergent manner from a common trivalent core containing three DMAP groups while a linear polymer was dendronized with aliphatic esters using a divergent growth scheme. Catalysis experiments clearly indicate that nanoenvironment plays the dominant role in determining the activity of the polymer catalysts, with the polyester platform being superior to the benzyl ether. Polymer architecture played little or no role in affecting catalysis. With respect to molecular transport and catalysis, this represents the first comparative study of the effect of architecture and nanoenvironment using structurally similar dendritic materials.
