Photochemical Nitrene Transfer Reactions of Iminoiodinanes with Sulfides

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Abstract: Photochemical, metal‐free nitrene transfer reactions for C−H amination, aziridination, or sulfilimination are highly desirable. Yet, photochemical sulfilimination reactions of nitrenes with sulfides are underdeveloped as singlet nitrene species would be required for a productive reaction. Herein, we describe the blue‐light‐mediated sulfilimination reaction using iminoiodinanes. We developed a protocol for a highly efficient stoichiometric reaction, which allows for the synthesis of sulfilimines in only 10 minutes reaction time. We further applied our reaction procedure towards allyl sulfides for the synthesis of sulfenamides in a sulfilimination/rearrangement cascade reaction. Moreover, we performed computational calculations and uncovered the participation of a singlet nitrene intermediate, which rapidly reacts with methyl phenyl sulfide to give the desired product.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Photochemical Nitrene Transfer Reactions of Iminoiodinanes with Sulfides ; day:10 ; month:02 ; year:2022 ; extent:1
ChemPhotoChem ; (10.02.2022) (gesamt 1)

Creator: Guo, Yujing
Pei, Chao
Empel, Claire
Jana, Sripati
Koenigs, Rene M.

DOI: 10.1002/cptc.202100293

URN: urn:nbn:de:101:1-2022021014242212486448

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:21 AM CEST

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Associated

Guo, Yujing
Pei, Chao
Empel, Claire
Jana, Sripati
Koenigs, Rene M.

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