56830-70-7Relevant articles and documents
Highly efficient and versatile acylation of alcohols with Bi(OTf)3 as catalyst
Orita, Akihiro,Tanahashi, Chiaki,Kakuda, Atsushi,Otera, Junzo
, p. 2877 - 2879 (2000)
A very convenient route for the acylation of alcohols is provide by using a Bi(OTf)3 catalyst [Eq. (1)]. In this protocol hindered and functionalized alcohols are acylated at 25°C, and solvents can be employed without purification. R= primary, secondary, tertiary alkyl, aryl; R'=Me, Ph, tBu.
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.
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.
