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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

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Chatterjee,  Sayanti
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi,  Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Laboratorium für Organische Chemie, ETH Zürich;

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Citation

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.


Cite as: https://hdl.handle.net/21.11116/0000-0007-AAD0-E
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.