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
Résumé
We report here the preparation of unprecedented analogues of 1,2-benzothiazine and benzoisothiazoleincorporating theS-trifluoromethyl sulfoximine group in their core. Using a stable precursor to start, cyclization occurs via acatalytic controlled process. The choice of the catalyst is crucial for selectivity toward thefive- or the six-membered ring.Interestingly, one of the benzothiazines can be converted on a gram scale into the trifluoromethylating Adachi reagent. We alsodisclose thefirst use of this reagent as a source of radical CF3under photoredox catalysis. DFT calculations were performed toclarify the cyclization mechanism.
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