Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst.
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 (approximately 80 degrees C). Chemoselective acetylation, pivalation, and benzoylation took place with acid-sensitive alcohols without any competitive dehydration/rearrangement.
Chakraborti
Asit K
AK
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar 160 062, Punjab, India. akchakraborti@niper.ac.in
Shivani
Shivani
S
D000107:Acetylation; D000215:Acylation; D000438:Alcohols / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007094:Imides / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010421:Pentanoic Acids / Q000737:chemistry; D013452:Sulfonium Compounds / Q000737:chemistry*
D000438:Alcohols; D000812:Anhydrides; D007094:Imides; D008698:Mesylates; D010421:Pentanoic Acids; D013452:Sulfonium Compounds; C005566:pivalic acid; D008274:Magnesium; C012077:trifluoromethanesulfonic acid