Study On Radical Cascade Reaction Of Alkynes With N-fluorobenzenesulfonimide

α-amino-α-aryl ketone is a key motif in various biologically active natural products andpharmaceuticals such as isothiocyanate, ketamine and prasugrel. They are also usefulprecursors for the synthesis of heterocycle. In most of the methods for the synthesis ofα-amino-α-aryl ketone, aryl or amino group was installed to the substruct respectively, causethe lose of the step economic and narrow scope of the substruct. Therefore, it is highlyappealing for the development of straightforward and facile synthetic strategy fromcommercial available chemicals under the mild conditions for these compounds.Alkyne functional group is ubiquitous in natural or synthetic compounds and alkynefunctionalization, the addition of functional groups across a triple bond, exemplifies a class ofreactions with significant synthetic potential. Nitrogen-containing organic compounds areprevalently important structural units found in natural and pharmaceutical products.Accordingly, aminative difunctionalization of alkynes, has become an important research fieldin organic chemistry, such as diamination, aminooxygenation, aminohalogenation,carboamination have been successfully developed. Radical cascade reactions of alkynes arevery synthetically attractive because they enable access to highly complex molecularskeletons in only few synthetic steps. The vast majority of synthetic work has been performedwith C-, Sn-and S-centered radicals, only very few examples of radical cascades that areinitiated by addition of N-centered radicals to alkynes have been reported. So thedevelopment of a “Cascade” radical reactions initiated by addition of N-centered radicals toalkynes are full of challenge.In this thesis, we present a novel aminative cascade radical reaction of alkynes tosynthesize α-amino-α-aryl ketone, using alcohol compounds as oxygen source and NFSI asoxidant, N-radical source and aryl source. The mechanism study indicates that the reactionmight proceed via cascade nitrogen-centered radical addition, aryl migration, desulfonylation,oxygenation and semi-pinacol rearrangement process to construct C–N, C–C（aryl）and C=Obonds for alkynes. This methodology provides a new facile and straightforward way for theα-amino-α-aryl ketones synthesize, especially for the construction of a quaternary carboncenter. To best of our knowledge, it is the first example to synthesis α-amino-α-aryl ketonesvia radical cascades addition to alkynes. This methodology provides a new way fordeveloping cascade reactions triggered by N-centered radical addition to alkynes.