23516-85-0Relevant articles and documents
Direct Synthesis of Tri-/Difluoromethyl Ketones from Carboxylic Acids by Cross-Coupling with Acyloxyphosphonium Ions
Ispizua-Rodriguez, Xanath,Munoz, Socrates B.,Krishnamurti, Vinayak,Mathew, Thomas,Prakash
supporting information, p. 15908 - 15913 (2021/10/07)
A simple and straightforward approach to the synthesis of trifluoromethyl and difluoromethyl ketones from widely available carboxylic acids is disclosed. The transformation utilizes an acyloxyphosphonium ion as the active electrophile, conveniently generated in situ from the carboxylic acid substrate by using commodity chemicals. The utility of the reaction system is exemplified by its chemoselectivity, with tolerance to a variety of important functional groups. The late-stage functionalization of carboxylic acid active pharmaceutical ingredients and pharmaceutically relevant compounds is also discussed.
Oxidation of alcohols using an oxoammonium salt bearing the nitrate anion
Miller, Shelli A.,Sandoval, Arturo León,Leadbeater, Nicholas E.
supporting information, (2019/12/25)
A methodology for the oxidation of alcohols to the corresponding carbonyl compounds is reported using a sub-stoichiometric quantity of an oxoammonium salt bearing the nitrate counterion. The approach proves successful for the oxidation of a range of alcohol substrates including those bearing an oxygen atom β to the site of oxidation or an α-trifluoromethyl moiety. The mechanism of the reaction has been probed and also gives an insight into the previously reported nitric acid mediated oxidation of alcohols.
Catalytic Oxidation of Alcohols Using a 2,2,6,6-Tetramethylpiperidine-N-hydroxyammonium Cation
Miller, Shelli A.,Bisset, Kathryn A.,Leadbeater, Nicholas E.,Eddy, Nicholas A.
supporting information, p. 1413 - 1417 (2019/01/04)
The oxidation of alcohols to aldehydes, ketones, and carboxylic acids is reported using 2,2,6,6-tetramethylpiperidine-4-acetamido-hydroxyammonium tetrafluoroborate as a catalyst in conjunction with sodium hypochlorite pentahydrate as a terminal oxidant. The reaction is generally complete within 30–120 min using an acetonitrile/water mix as the solvent, and no additives are required. Product yields are good to excellent and of particular note is that the methodology can be used to access aryl α-trifluoromethyl ketones.