American Chemical Society
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Gold-Catalyzed [3,3]-Sigmatropic Rearrangement of ortho-Alkynyl‑S,S‑diarylsulfilimines

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journal contribution
posted on 2023-04-18, 17:40 authored by Alexandra V. Mackenroth, Patrick W. Antoni, Frank Rominger, Matthias Rudolph, A. Stephen K. Hashmi
Highly functionalized 5H-pyrrolo[2,3-b]pyrazine cores, carrying a diaryl sulfide moiety at the C-7 position, were obtained from a gold-catalyzed reaction using easily accessible ortho-alkynyl-substituted S,S-diarylsulfilimines as intramolecular nitrene transfer reagents for the first time. The reaction proceeds under mild conditions, providing excellent yields while tolerating a large variety of different substitution patterns. We provide experimental evidence for an intramolecular reaction mechanism, likely including an unprecedented gold-catalyzed amino sulfonium [3,3]-sigmatropic rearrangement.