Divergent Synthesis of 1,2-Benzo[e]thiazine and Benzo[d]thiazole Analogues Containing a S-Trifluoromethyl Sulfoximine Group: Preparation and New Properties of the Adachi Reagent

Abstract

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Synthesis of S‐Trifluoromethyl S‐Arylsulfoximine Thioglycosides through Pd‐Catalyzed Migita Cross‐Coupling

“…To reach our synthetic goal, we planned an approach merging the knowledge of both of our research groups: in the chemistry of S‐trifluoromethyl sulfoximine and in the development of strategies devoted to the reactivity of thiosugars under transition metal‐catalysis including Pd‐catalyzed Migita cross‐coupling. The synthesis of o ‐iodo S‐aryl S‐trifluoromethylsulfoximine and the subsequent selective functionalization of the ortho position, in the presence of the free NH sulfoximine was recently carried out . Another interest of the present study would rely on the chiral pool offered by the thiosugars derivatives.…”

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes†

“…In 2019, Miqueu and Magnier showed the preparation of Adachi's reagent by Sonogashira and cyclization processes (Scheme 5a). [ 42 ] The choice of the catalyst at the cyclization is crucial for selectivity toward the five‐ or six‐membered ring. A 14‐membered enediyne‐embedded macrocycle can also be prepared via sequential Ugi/Sonogashira/macrolactonization reactions.…”

Benzodithiazoles‐Sulfoximines: Preparation, Properties and Reactivities as Radical Perfluoroalkylating Agents

“…[15] In this context, we developed in 2019, a synthesis and the use in photoredox catalysis, of the Adachi reagent 5 which was never used, to the best of our knowledge, in an academic work. [16] Our group also succeeded to prepare an original hypervalent compound 8 as an analogue of the Togni reagent 3 (Figure 1a). [17] We have demonstrated the enhanced reactivity of derivative 8 compared to the parent compound 3 in the direct trifluoromethylation of alcohols.…”