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  Hydroxylamine‐Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron‐Catalyzed Preparation of Unprotected Sulfinamides from Thiols

Chatterjee, S., Makai, S., & Morandi, B. (2021). Hydroxylamine‐Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron‐Catalyzed Preparation of Unprotected Sulfinamides from Thiols. Angewandte Chemie International Edition, 60(2), 758-765. doi:10.1002/anie.202011138.

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 Creators:
Chatterjee, Sayanti1, Author              
Makai, Szabolcs2, Author
Morandi, Bill1, 2, Author              
Affiliations:
1Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              
2Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland, ou_persistent22              

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Free keywords: amino oxidation; iron; sulfinamides; sustainable catalysis; thiols
 Abstract: An iron catalyzed reaction for the selective transformation of thiols (‐SH) to sulfinamides (‐SONH2) by a direct transfer of ‐O and free ‐NH2 groups has been developed. The reaction operates under mild conditions using a bench stable hydroxylamine derived reagent, exhibits broad functional group tolerance, is scalable and proceeds without the use of any precious metal catalyst or additional oxidant. This novel, practical reaction leads to the formation of two distinct new bonds (S=O and S−N) in a single step to chemoselectively form valuable, unprotected sulfinamide products. Preliminary mechanistic studies implicate the role of the alcoholic solvent as an oxygen atom donor.

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Language(s): eng - English
 Dates: 2020-09-212021-01-11
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202011138
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 60 (2) Sequence Number: - Start / End Page: 758 - 765 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851