Iron(III) tosylate catalyzed acylation of alcohols, phenols, and aldehydes

• Published in: Tetrahedron letters Vol. 53; no. 51; pp. 6946 - 6949
• Main Authors: Baldwin, Neil J., Nord, Anna N., O’Donnell, Brendan D., Mohan, Ram S.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 19.12.2012; Elsevier
• Subjects: Acetylation; Acylation; Alcohols; Aldehydes; Catalysts; Chemistry; Chemistry, Organic; Diols; Esters; Green chemistry; Iron and its compounds; Phenols; Physical Sciences; Science & Technology; Tetrahedrons; Phenols; Esters; Green chemistry; Diols; Iron and its compounds; Acylation; Alcohols; ORGANIC-SYNTHESIS; ACETYLATION; CHEMOSELECTIVE SYNTHESIS; IONIC LIQUID; DEPROTECTION; HIGHLY EFFICIENT; EFFICIENT CATALYST; SOLVENT-FREE; RECYCLABLE CATALYST; HOMOALLYL ETHERS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2012.10.033

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 2.0mol% 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 5.0mol% 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.