Mechanochemical Iron‐Catalyzed Nitrene Transfer Reactions : Direct Synthesis of N‐Acyl Sulfonimidamides from Sulfinamides and Dioxazolones
Pan, S., Mulks, F., Wu, P., Rissanen, K., & Bolm, C. (2024). Mechanochemical Iron‐Catalyzed Nitrene Transfer Reactions : Direct Synthesis of N‐Acyl Sulfonimidamides from Sulfinamides and Dioxazolones. Angewandte Chemie, 63(5), Article e202316702. https://doi.org/10.1002/anie.202316702
Published in
Angewandte ChemieDate
2024Copyright
© 2023 The Authors. Angewandte Chemie International Edition
published by Wiley-VCH GmbH.
A mechanochemical synthesis of sulfonimidamides by iron(II)-catalyzed exogenous ligand-free N-acyl nitrene transfer to sulfinamides is reported. The one-step method tolerates a wide range of sulfinamides with various substituents under solvent-free ambient conditions. Compared to its solution-phase counterpart, this mechanochemical approach shows better conversion and chemoselectivity. Mechanistic investigations by ESI-MS revealed the generation of crucial nitrene iron intermediates.
Publisher
Wiley-VCH VerlagISSN Search the Publication Forum
1433-7851Publication in research information system
https://converis.jyu.fi/converis/portal/detail/Publication/194896868
Metadata
Show full item recordCollections
Additional information about funding
S.P. and P.W. thank to the China Scholarship Council (CSC) for predoctoral stipends. F.F.M. is grateful to the Fonds der Chemischen Industrie for a Liebig Fellowship (Li 210/01).License
Related items
Showing items with similar title or keywords.
-
1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions
Schöbel, Jan-Hendrik; Elbers, Philipp; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten (Wiley-VCH Verlag, 2021)Three‐dimensional aza‐analogues of 1,2‐benzothiazine 1,1‐dioxides have been prepared from sulfonimidamides. Two different protocols are presented. The first is a rhodium‐catalyzed annulation reaction with alpha‐sulfonyloxyketones ... -
Cyclic Sulfoximine and Sulfonimidamide Derivatives by Copper‐Catalyzed Cross‐Coupling Reactions with Elemental Sulfur
Wu, Peng; Ward, Jas S.; Rissanen, Kari; Bolm, Carsten (Wiley, 2023)Copper-catalyzed cross-coupling reactions of α-bromoaryl NH-sulfoximines with elemental sulfur lead to benzo[d][1,3,2]dithiazole-1-oxides, which represent a new class of three-dimensional heterocycles. The reactions proceed ... -
A Copper‐Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine‐1‐oxides
Hommelsheim, Renè; Bausch, Sandra; Selvakumar, Arjuna; Amer, Mostafa M.; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten (Wiley-VCH Verlag, 2023)Copper(I)-catalyzed domino reactions of 2-azido sulfoximines with 1-iodoalkynes yield fused triazolyl-containing benzothiadiazine-1-oxides. The protocol features the synthesis of two fused heterocyclic rings in one step ... -
Chemoselective heterogeneous iridium catalyzed hydrogenation of cinnamalaniline
Savela, Risto; Shcherban, Nataliya D.; Melander, Marko M.; Bezverkhyy, Igor; Simakova, Irina L.; Långvik, Otto; Kholkina, Ekaterina; Schindler, Tamara; Krauβ, Annabelle; Honkala, Karoliina; Murzin, Dmitry Yu.; Leino, Reko (Royal Society of Chemistry, 2021)Selective hydrogenation of unsaturated imines over heterogeneous catalysts is an ecologically feasible and effective way to produce commercially valuable saturated imines and unsaturated amines under mild conditions, ... -
N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines : synthesis, X-ray crystallography, and halogen bonding
Schumacher, Christian; Fergen, Hannah; Puttreddy, Rakesh; Truong, Khai-Nghi; Rinesch, Torsten; Rissanen, Kari; Bolm, Carsten (Royal Society of Chemistry, 2020)In the presence of KOH, NH-sulfoximines react with pentafluoropyridine to give N-(tetrafluoropyridyl)sulfoximines (NTFP-sulfoximines) in moderate to excellent yields. Either a solution-based or a superior solvent-free ...