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Consecutive O−S/N−S Bond Cleavage in Gold‐Catalyzed Rearrangement Reactions of Alkynyl N ‐Sulfinylimines
Author(s) -
Tashiro Hiroki,
Terada Masahiro,
Nakamura Itaru
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202100207
Subject(s) - azirine , carbene , chemistry , moiety , catalysis , ring (chemistry) , cleavage (geology) , oxygen atom , medicinal chemistry , bond cleavage , stereochemistry , photochemistry , organic chemistry , molecule , materials science , fracture (geology) , composite material
Gold‐catalyzed reactions of alkynyl N ‐sulfinylimines were used to produce the corresponding 2 H ‐azirines possessing sulfenyl and acyl groups at the 3‐position of the azirine ring in good to excellent yields. These reactions involved internal transfer of the sulfinyl oxygen atom to form a thiooxime intermediate tethered to an α‐oxo gold carbene moiety. Subsequent insertion of the carbene into the N−S bond resulted in ring construction.