Consecutive O−S/N−S Bond Cleavage in Gold‐Catalyzed Rearrangement Reactions of Alkynyl  N ‐Sulfinylimines | Zendy

Tashiro Hiroki | Zendy; Terada Masahiro | Zendy; Nakamura Itaru | Zendy

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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.

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