Cyclic Sulfoximine and Sulfonimidamide Derivatives by Copper‐Catalyzed Cross‐Coupling Reactions with Elemental Sulfur
Wu, P., Ward, J. S., Rissanen, K., & Bolm, C. (2023). Cyclic Sulfoximine and Sulfonimidamide Derivatives by Copper‐Catalyzed Cross‐Coupling Reactions with Elemental Sulfur. Advanced Synthesis and Catalysis, 365(4), 522-526. https://doi.org/10.1002/adsc.202201408
Published in
Advanced Synthesis and CatalysisDate
2023Copyright
© 2023 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH
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 under mild conditions showing good functional group and heterocycle tolerance. By imination/oxidation, the initial cross-coupling products can be converted to unprecedented cyclic sulfonimidamides derivatives. Furthermore, a seven-membered heterocycle was obtained by a ruthenium-catalyzed ring-expansion with ethyl propiolate.
Publisher
WileyISSN Search the Publication Forum
1615-4150Keywords
Publication in research information system
https://converis.jyu.fi/converis/portal/detail/Publication/177039584
Metadata
Show full item recordCollections
Additional information about funding
P. W. is grateful to the China Scholarship Council (CSC) for a predoctoral stipend, and we acknowledge the Alexander von Humboldt Foundation for support of K. R. (AvH research award). Open Access funding enabled and organized by Projekt DEAL.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 ... -
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 ... -
Mechanochemical Iron‐Catalyzed Nitrene Transfer Reactions : Direct Synthesis of N‐Acyl Sulfonimidamides from Sulfinamides and Dioxazolones
Pan, Shulei; Mulks, Florian; Wu, Peng; Rissanen, Kari; Bolm, Carsten (Wiley-VCH Verlag, 2024)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 ... -
Synthesis of N‐Fused Indolines via Copper (II)‐Catalyzed Dearomatizing Cyclization of Indoles
Zhang, Jingyu; Xia, Wei; Huda, Saskia; Ward, Jas S.; Rissanen, Kari; Albrecht, Markus (Wiley, 2021)Herein, a copper(II)-catalyzed dearomative cyclization amination of N-(2-aminobenzoyl) indoles is presented. Under mild reaction conditions, the cyclization proceeds to afford tetracyclic indolines by forming a new C−N ... -
Carboxylate catalyzed isomerization of β,γ‐unsaturated N-acetylcysteamine thioesters
Riuttamäki, Saara; Laszkó, Gergely; Madarász, Ádam; Földes, Tamás; Pápai, Imre; Bannykh, Anton; Pihko, Petri M. (Wiley-VCH Verlag, 2022)We demonstrate herein the capacity of simple carboxylate salts – tetrametylammonium and tetramethylguanidinium pivalate – to act as catalysts in the isomerization of β,γ-unsaturated thioesters to α,β-unsaturated thioesters. ...