An oxidative and acid-free method for the nitration of N-aryl sulfonamides has been developed using a combination of sodium nitrite as cheap and easy to handle NO2-source and the hypervalent iodine reagent PIFA as stoichiometric oxidant. Under very mild reaction conditions, the desired mononitrated aryl sulfonamides were isolated in up to 87% yield. This is the first example of an iodane-mediat...

Treatment of oximes with hypervalent iodine leads to substituted isoxazoles via rapid formation of nitrile oxides. Reaction with terminal alkynes led to a series of 3,5-disubstituted isoxazoles with complete regioselectivity and high yield, in a procedure mild enough to prepare a range of nucleoside and peptide conjugates. Exceptionally high reaction rates were found for the formation of 3,4,5-...

The clean and facile electrochemical synthesis of hypervalent iodine reagents is a fast growing field. In the past 5 years, diverse number reaction types have been established, from fluorinations, oxidative cyclizations, C−N C−H couplings oxidations. Electrochemistry beneficial in terms sustainability as requirement for chemical oxidants eliminated. This contributes to cleaner processes with li...

The direct oxidative coupling reaction has been an attractive tool for environmentally benign chemistry. Reported herein is that the hypervalent iodine catalyzed oxidative metal-free cross-coupling reaction of phenols can be achieved using Oxone as a terminal oxidant in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). This method features a high efficiency and regioselectivity, as well as functional-g...

Cyclic unsaturated ketone frameworks, which are obtained as the dearomatized products of phenols and their derivatives, valuable to synthesis complex molecules also contribute generation that can be readily employed for further transformations. Herein, use hypervalent iodine compounds access enantioenriched through direct stepwise dearomatization reactions have been elaborated. More information...

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34–81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. transformation probably proceeds throug...