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Catalytic Regio‐ and Stereoselective Alkene Sulfenoamination for 1,4‐Benzothiazine Synthesis
Author(s) -
Alom NurE.,
Kaur Navdeep,
Wu Fan,
Saluga Shan Jasmine,
Li Wei
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900549
Subject(s) - alkene , benzothiazine , chemistry , catalysis , reagent , stereoselectivity , iodide , combinatorial chemistry , organic chemistry
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.