A synthesis of a wide range of different aliphatic, aromatic, and heterocyclic N-(trifluoromethyl)amides along with aromatic N-(difluoromethylene)-N-(trifluoromethyl)amine derivatives has been developed. The starting materials are the easily available isothiocyanates, and the fluorinating reagent is the commercially available bromine trifluoride. The reaction is performed under mild conditions, and the fluorinated amides and amines are produced in moderate to high yields.
A mild and very efficient method for converting boronic acids to alcohols has been developed using the acetonitrile complex of hypofluorous acid HOF·CH3CN. Employing (18)O-labeled water results in alcohols containing a heavy oxygen isotope. The reactions were performed at room temperature, within a few minutes and in excellent yields.
Aryl boronic acids or pinacol esters containing EDG were converted in good yields and fast reactions to the corresponding aryl fluorides using the readily obtainable solutions of AcOF. In reactions with aryl boronic acids containing EWG at the para position, there are two competing forces: one directing the fluorination to take place ortho to the boronic acid and the other, toward an ipso substitution. With EWG meta to the boronic acid, substitution ipso to the boron moiety takes place in good yields.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.