Catalytic Regio‐ and Stereoselective Alkene Sulfenoamination for 1, 4‐Benzothiazine Synthesis. Issue 28 (2nd May 2019)

• Record Type: Journal Article
• Authors: Alom, Nur‐E.; Kaur, Navdeep; Wu, Fan; Saluga, Shannon Jasmine; Li, Wei
• Is Part Of: Chemistry. Volume 25:Issue 28(2019)
• Page Start: 6902
• Page End: 6906
• Publication Date: 2019-05-02
• Subjects: alkene sulfenoamination -- 1, 4-benzothiazines -- heterocycles -- iodide catalysis -- thiiranium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201900549
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: An alkene sulfenoamination reaction with 2‐aminothiophenol is developed using iodide catalysis. This reaction renders access to useful 1, 4‐benzothiazines with good functional group compatibility including both electron‐donating and electron‐withdrawing substituents. The reaction is proposed to proceed through an inversion of the polarity of the thiol functionality. Our mechanistic studies reveal that both thiiranium and thiyl radical pathways are plausible and that the disulfide reagent can also function as a viable substrate in this reaction. Abstract : Easy access to heterocycles ! A novel catalytic strategy is introduced to couple alkenes and unfunctionalized thioamines for the synthesis of useful heterocycles. This protocol tolerates a wide range of substrates with great regioselectivity and diastereoselectivity.