13080-43-8Relevant academic research and scientific papers
Na 2 CO 3-Catalyzed O-Acylation of Phenols for the Synthesis of Aryl Carboxylates with Use of Alkenyl Carboxylates
Zhou, Xiao-Yu,Chen, Xia
supporting information, p. 2321 - 2325 (2018/10/20)
Inorganic base-catalyzed O-acylation of phenol and its derivatives has been developed. The procedure provides an efficient catalysis system for the preparation of aryl carboxylates with alkenyl carboxylates as acyl reagents. The reaction proceeded smoothly by using ?-Na 2 CO 3 as the catalyst in MeCN to produce the corresponding aryl carboxylates in good to excellent yields.
An extremely efficient and green method for the acylation of secondary alcohols, phenols and naphthols with a deep eutectic solvent as the catalyst
Nguyen, Hai Truong,Tran, Phuong Hoang
, p. 98365 - 98368 (2016/10/31)
The typical deep eutectic solvent [CholineCl][ZnCl2]3, easily prepared from choline chloride and zinc chloride, is green and useful for the acylation of secondary alcohols, phenols, and naphthols with acid anhydrides. Its efficiency allows the acylation of sterically hindered secondary alcohols and acid anhydrides to proceed in high yield under mild condition. The catalyst is cheap, easy to handle, conveniently synthesized in a single step, and recyclable for several times without significant loss of catalytic activity.
Palladium-Catalyzed Desilylative Acyloxylation of Silicon-Carbon Bonds on (Trimethylsilyl)arenes: Synthesis of Phenol Derivatives from Trimethylsilylarenes
Gondo, Keisuke,Oyamada, Juzo,Kitamura, Tsugio
supporting information, p. 4778 - 4781 (2015/10/12)
A strategy for desilylative acetoxylation of (trimethylsilyl)arenes has been developed in which (trimethylsilyl)arenes are converted into acetoxyarenes. The direct acetoxylation is performed in the presence of 5 mol % of Pd(OAc)2 and PhI(OCOCF3)2 (1.5 equiv) in AcOH at 80°C for 17 h. The acetoxyarenes are obtained in good to high yields (67-98%). The synthetic utility is demonstrated with a one-pot transformation of (trimethylsilyl)arenes to phenols by successive acetoxylation and hydrolysis. Furthermore, desilylative acyloxylation of 2-(trimethylsilyl)naphthalene using several carboxylic acids has been conducted.
Asymmetric cycloadditions of o-quinone methides employing chiral ammonium fluoride precatalysts
Alden-Danforth, Ethan,Scerba, Michael T.,Lectka, Thomas
supporting information; experimental part, p. 4951 - 4953 (2009/05/31)
(Chemical Equation Presented) The catalytic, enantioselective, [4+2] cycloaddition reaction of ortho-quinone methides with silyl ketene acetals is described. This mechanistically interesting reaction, initiated by a chiral cinchona alkaloid-derived ammonium fluoride "precatalyst" complex, affords a variety of alkyl- and aryl-substituted 3,4-dihydrocoumarin products in excellent yield and with good enantioselectivity.
Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst
Chakraborti, Asit K.,Shivani
, p. 5785 - 5788 (2007/10/03)
Magnesium bistrifluoromethanesulfonimide catalyzed the acetylation of phenols, alcohols, and thiols under solvent-free conditions at room temperature and in short times. Electron-deficient and sterically hindered phenols provided excellent yields. The catalyst was found to be general for acylation with other anhydrides, such as propionic, isobutyric, pivalic, chloroacetic, and benzoic anhydrides. The rate of acylation was influenced by the electronic and steric factors associated with the anhydride. The reaction with less electrophilic anhydrides (e.g., chloroacetic and benzoic anhydrides) required higher temperature (～80 °C). Chemoselective acetylation, pivalation, and benzoylation took place with acid-sensitive alcohols without any competitive dehydration/rearrangement.
Copper(II) Tetrafluoroborate-Catalyzed Acetylation of Phenols, Thiols, Alcohols, and Amines
Chakraborti, Asit K.,Gulhane, Rajesh,Shivani
, p. 111 - 115 (2007/10/03)
Copper(II) tetrafluoroborate efficiently catalyzes acetylation of structurally diverse phenols, alcohols, thiols, and amines with stoichiometric amounts of Ac2O under solvent-free conditions at room temperature. Acid-sensitive alcohols are smoothly acetylated without competitive side reactions. The reaction is influenced by the steric and electronic factors associated with the substrate as well as the anhydride. Acetylation of a sterically hindered substrate requires excess of anhydride and longer time. Acylation with less electrophilic anhydrides affords poor to moderate yields.
Electrostatic catalysis by ionic aggregates: Scope and limitations of Mg(ClO4)2 as acylation catalyst
Chakraborti, Asit K.,Sharma, Lalima,Gulhane, Rajesh,Shivani
, p. 7661 - 7668 (2007/10/03)
Alkali and alkaline earth metal perchlorates exhibit electrostatic catalysis in the activation of anhydrides for the acylation reaction. Perchlorates with higher values of the charge-size function of the metal ion exhibit better catalytic activity following the order Mg(ClO4) 2>Ba(ClO4)2>LiClO4. Acylation of structurally diverse phenols, thiols, alcohols, and amines have been carried out with stoichiometric amounts of anhydride at room temperature under solvent free conditions in the presence of catalytic amount of Mg(ClO4) 2. Sterically hindered and electron deficient phenols are efficiently acylated. Acylation with sterically hindered anhydrides such as iso-butyric, pivalic, and benzoic anhydrides are carried out with phenols and alcohols in excellent yields. Acid-sensitive alcohols are acylated in excellent yields without any competitive side reactions.
Indium(III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines
Chakraborti, Asit K.,Gulhane, Rajesh
, p. 6749 - 6753 (2007/10/03)
Indium(III) chloride efficiently catalyses the acylation of structurally diverse phenols, alcohols, thiols, and amines under solvent free conditions. Acid sensitive alcohols are smoothly acylated without competitive side reactions. Acylation of 2-hydroxynaphthalene is carried out with carboxylic acids adopting the mixed anhydride protocol using trifluoroacetic anhydride.
Sodium Borohydride-Carboxylic Acid Systems - A new Method of Acylation of Alcohols, Phenols and Thiophenols
Prashad, Mahavir,Jigajinni, Veerappa B.
, p. 822 - 823 (2007/10/02)
A new method of acylation of alcohols, phenols and thiophenols in sodium borohydride-carboxylic acid system is described.A plausible mechanism of this acylation through tetraacyloxyborate derivative has been postulated.
