Strategic Synthesis of Sulfinamides as Versatile S(IV) Intermediates DOI Creative Commons
Subham Das,

Amit Dhibar,

Basudev Sahoo

et al.

ACS Organic & Inorganic Au, Journal Year: 2024, Volume and Issue: 5(1), P. 1 - 12

Published: Nov. 30, 2024

Sulfinamides constitute adaptable S(IV) intermediates with a sulfur stereocenter, having emerging interest in divergent synthesis of high-valent S(VI) functional bioisosteres. Recent years have witnessed the strategic development mild and selective synthetic routes for highly functionalized sulfinamides, employing stable organometallic reagents, carbon-centered radical precursors, other abundant coupling partners merged various reagents arena metal, photoredox, organocatalysis. Furthermore, asymmetric metal organocatalysis enabled stereoselective enantioenriched sulfinamides. In this Perspective, we present recent (2021 to present) advancement methods toward

Language: Английский

The Catalytic Synthesis of Aza-Sulfur Functional Groups DOI
Michael C. Willis,

Ming-Kai Wei

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 26, 2024

Abstract Sulfur-containing compounds are found in myriad applications. Sulfones and sulfonamides the most common functional groups used medicinal agrochemical endeavours. Isosteres of these groups, for example, sulfoximines sulfonimidamides, emerging functionalities, they increasingly relevant patent literature. However, general, associated synthetic routes still have limitations, including use harsh reaction conditions highly reactive reagents. A variety catalytic reactions that employ a diverse range substrate classes been developed to address issues. This short review highlights recent syntheses aza-sulfur compounds, which we hope will open new directions discovery chemistry. 1 Introduction 2 Reactions N-Sulfinylamines 3 with Sulfenamides 4 Sulfinates 5 Sulfinamides 6 Other Aza-Sulfur Compounds 7 Conclusion

Language: Английский

Citations

4
Trendbericht Anorganische Chemie 2024: Hauptgruppen‐ und Molekülchemie DOI Open Access
Josh Abbenseth, Frank Tambornino

Nachrichten aus der Chemie, Journal Year: 2025, Volume and Issue: 73(2), P. 46 - 55

Published: Jan. 31, 2025

Abstract Das erste heterobimetallische Dimetallocen; mit sterisch anspruchsvollen Liganden lassen sich einfach‐koordinierte Hauptgruppenverbindungen der Gruppen 13 bis 15 herstellen; neue Diazoverbindungen erlauben es, B‐R‐Einheiten und Kohlenstoffatome zu übertragen.

Citations

0
Palladium-Catalyzed Addition of Aryl Halides to N-Sulfinylamines for the Synthesis of Sulfinamides DOI Creative Commons

Ming-Kai Wei,

Daniel. F. Moseley,

Robin M. Bär

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(29), P. 19690 - 19695

Published: July 12, 2024

Sulfinamides are versatile, synthetically useful intermediates, and final motifs. Traditional methods to synthesize sulfinamides generally require substrates with preinstalled sulfur centers. However, these precursors have limited commercial availability, the associated synthetic routes often harsh reaction conditions highly reactive reagents, thus severely limiting their application. Herein, we report synthesis of from aryl alkenyl (pseudo)halides N-sulfinylamines, enabled by palladium catalysis. The reactions use mild achieved without preformed organometallic resulting in transformations broad generality high functional group tolerance. In particular, featuring protic electrophilic groups can be used successfully. modification complex cores natural product derivatives demonstrates utility this method.

Language: Английский

Citations

3
Thionyl Fluoride as a Sulfur(IV) SuFEx Hub for the Efficient Syntheses of Sulfinamides and Sulfinate Esters DOI

William P. Chappell,

Marie Favié,

Glenn M. Sammis

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(72), P. 9765 - 9768

Published: Jan. 1, 2024

Herein, we demonstrate a method for the syntheses of sulfinamides and sulfinate esters using novel sulfur(IV) fluoride exchange reaction with organometallic reagents. Our strategy involves addition an amine or alcohol nucleophile to thionyl fluoride, acting as S(IV) SuFEx hub, followed by reagent. This approach allows efficient access (45-91% yields) (44-82% in only 30 minutes. The sulfinamide also can be readily derivatized corresponding S(VI) sulfonamides, sulfonate esters, sulfonimidamides, sulfonimidates without isolation intermediates.

Language: Английский

Citations

2
Synthesis of Thiourea and Thioamide S-Oxides via SO Transfer from a Thiirane S-Oxide onto N-Heterocyclic Carbenes DOI
Serhii Medvedko, Markus Ströbele,

M.H. Fechter

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5868 - 5872

Published: July 1, 2024

Thiourea S-oxides are labile compounds that suffer from a quick overoxidation when directly prepared thioureas. Therefore, we have developed an alternative route on the basis of SO transfer thiirane S-oxide onto sterically encumbered N-heterocyclic carbenes, including imidazole- and imidazoline-ylidenes, cyclic alkyl amino carbene. Reaction conditions DFT computations suggest concerted mechanism. nucleophiles adding to dimethyl acetylenedicarboxylate under fission S–O bond.

Language: Английский

Citations

1
Facile synthesis of vinyl sulfoxides via external oxidant-free oxidative condensation of phenylglycinols with DMSO DOI
Xiaofan Shi,

Rongkang Zhang,

Chuang Liu

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 151, P. 155321 - 155321

Published: Oct. 11, 2024

Language: Английский

Citations

0
(((2S,3R)‐2,3‐Diphenylaziridin‐1‐yl)imino)‐ λ 4‐sulfanone DOI
Fumito Saito

Encyclopedia of Reagents for Organic Synthesis, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 2

Published: Nov. 30, 2024

image [3003056‐18‐3] C 14 H 12 N 2 OS (MW 256.32) InChI = 1S/C14H12N2OS/c17‐18‐15‐16‐13(11‐7‐3‐1‐4‐8‐11)14(16)12‐9‐5‐2‐6‐10‐12/h1‐10,13‐14H/t13‐,14+,16? InChIKey NPPOMHKZTUKVAS‐MZBDJJRSSA‐N (reagent used as an –S(O)– building block donor for the synthesis of sulfoxides and sulfinamides 1 ) Physical Data: mp 74–75 °C (decomposed). Solubility: soluble in benzene, chloroform, DMSO, ether, THF, toluene. Form Supplied in: white to pale yellow solid, not commercially available. cis ‐Stilbene is a typical impurity. Analysis Reagent Purity: reagent purity determined by NMR spectroscopy. Preparative Methods: prepared three steps from available ‐stilbene ‐aminophthalimide. The preparation ‐2,3‐diphenyl‐1‐aziridinamine carried out oxidative cyclization 3 hydrazinolysis. free hydrazine treated with thionyl chloride presence triethylamine yield sulfinylhydrazine ( ). After workup, high without further purification. Impure samples cannot typically be upgraded any traditional methods. Handling, Storage, Precautions: store neat, refrigerate, inert atmosphere. Can stored at least one month −20 °C. At room temperature, sample gradually changes into sticky solid over week, likely because formation ‐stilbene.

Language: Английский

Citations

0
Strategic Synthesis of Sulfinamides as Versatile S(IV) Intermediates DOI Creative Commons
Subham Das,

Amit Dhibar,

Basudev Sahoo

et al.

ACS Organic & Inorganic Au, Journal Year: 2024, Volume and Issue: 5(1), P. 1 - 12

Published: Nov. 30, 2024

Sulfinamides constitute adaptable S(IV) intermediates with a sulfur stereocenter, having emerging interest in divergent synthesis of high-valent S(VI) functional bioisosteres. Recent years have witnessed the strategic development mild and selective synthetic routes for highly functionalized sulfinamides, employing stable organometallic reagents, carbon-centered radical precursors, other abundant coupling partners merged various reagents arena metal, photoredox, organocatalysis. Furthermore, asymmetric metal organocatalysis enabled stereoselective enantioenriched sulfinamides. In this Perspective, we present recent (2021 to present) advancement methods toward

Language: Английский

Citations

0