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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
Author(s) -
Chatterjee Sayanti,
Makai Szabolcs,
Morandi Bill
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202011138
Subject(s) - hydroxylamine , chemistry , reagent , catalysis , functional group , combinatorial chemistry , solvent , reaction conditions , dual role , organic chemistry , polymer
An iron catalyzed reaction for the selective transformation of thiols (‐SH) to sulfinamides (‐SONH 2 ) by a direct transfer of ‐O and free ‐NH 2 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.