Synthesis of Sulfilimines via Visible‐Light‐Mediated Triplet Energy Transfer to Sulfonyl Azides DOI
Norihito Arichi,

Tsuyoshi Amano,

Shuhan Wu

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(48)

Published: June 24, 2024

Abstract Sulfilimines and their derivatives have garnered considerable interest in both synthetic medicinal chemistry. Photochemical nitrene transfer to sulfides is known as a conventional approach sulfilimines. However, the existing methods limited substrate scope stemming from incompatibility of singlet intermediates with nucleophilic functional groups. Herein, we report synthesis N ‐sulfonyl sulfilimines via visible‐light‐mediated energy sulfonyl azides, uncovering previously overlooked reactivity triplet nitrenes sulfides. This reaction features broad group tolerance, water compatibility, amenability late‐stage functionalization drugs. Thus, this work represents an important example chemistry that overcomes challenges traditional methods.

Language: Английский

Copper-Catalyzed Aerobic S-Amination of Sulfenamides for the Synthesis of Sulfinamidines DOI
Guoling Huang,

Jianlin Ye,

Minxi Tan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(23), P. 16116 - 16121

Published: Nov. 20, 2023

Herein, we present a copper-catalyzed oxidative amination of sulfenamides for the synthesis sulfinamidines. By employment air as terminal oxidant, diverse array secondary and primary amines can be efficiently transformed into their corresponding products. This method is well-suited last-stage functionalization, underlying mechanism has been investigated. The transformation characterized by exceptional chemoselectivity, mild conditions, facile operation, broad substrate compatibility, which have significant implications fields pharmaceuticals organic synthesis.

Language: Английский

Citations

11
Overlooked aza-S(iv) motifs: synthesis and transformations of sulfinamidines and sulfinimidate esters DOI
Michael Andresini, Marco Colella, Leonardo Degennaro

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(38), P. 7681 - 7690

Published: Jan. 1, 2023

Significant advancements have recently been made in the chemistry of sulfinamidines and sulfinimidate esters. This review aims to provide an overview synthetic methods for preparation transformation these overlooked compounds.

Language: Английский

Citations

10
Trends and Challenges in Electrifying Technical Organic Synthesis DOI Creative Commons
Philipp Röse,

Paul Neugebauer,

Siddharth Tamang

et al.

Chemie Ingenieur Technik, Journal Year: 2025, Volume and Issue: unknown

Published: March 18, 2025

Abstract Organic electrosynthesis is a potential enabler for the energy and resource transition in chemical industry as it offers sustainable alternative to homogeneous or heterogeneous processes producing fine commodity chemicals. It utilizes electricity instead of hazardous reagents and, thus, also allows reducing product's carbon footprint waste production. enables dynamic operation safe due galvanostatic process control. Electro‐organic are not yet widespread. Engineering tools have been tailored electro‐organic processes, more quantitative model‐based insight needed. Extensive adoption requires efforts regarding electrode material performance stability, scalable reactor design, digitization. Addressing these issues interdisciplinary collaboration, particularly between chemists engineers, accelerate implementation with high efficiency economic feasibility.

Language: Английский

Citations

0
Mechanochemical syntheses of N-acyl sulfinamidines via iron-nitrenoids and their conversions to sulfur(VI) derivatives DOI Creative Commons

Shulei Pan,

Peng Wu, Yijie Hu

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

Citations

0
Electrochemical Conversions of Sulfenamides into Sulfonimidoyl- and Sulfondiimidoyl Fluorides DOI Creative Commons
Bin Zhao,

Diping Zeng,

Xinglei He

et al.

JACS Au, Journal Year: 2025, Volume and Issue: unknown

Published: April 29, 2025

Language: Английский

Citations

0
Electrochemically Promoted Synthesis of N-Sulfonyl Sulfinimidate Esters and Sulfilimines from Sulfonamides, Thiophenols, Thioethers, and Alcohols DOI

A. Chen,

Yan He, Zhang Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 9, 2025

In this work, we report an electrochemical method for the straightforward preparation of scarcely accessible sulfinimidate esters from readily available sulfonamides, thiophenols, and alcohols. Mechanistic experiments show that sulfur oxidation at anodic surface generates electrophilic intermediate, which subsequently undergoes nucleophilic substitution. Moreover, sulfilimines can be obtained in moderate-to-excellent yields when thioethers are used as S-donor instead thiophenols via a dehydrogenateive imination process. This is also characterized by mild reaction condition, operational simplicity, high atomic economic efficiency, easy later drug synthesis, modification, well scaling up to gram scale.

Language: Английский

Citations

0
Efficient and Sustainable Electrosynthesis of N-Sulfonyl Iminophosphoranes by the Dehydrogenative P–N Coupling Reaction DOI Creative Commons

Jessica C. Bieniek,

Darryl Nater,

Sara L. Eberwein

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(6), P. 2188 - 2196

Published: April 18, 2024

Iminophosphoranes are commonly used reagents in organic synthesis and are, therefore, of great interest. An efficient sustainable iodide-mediated electrochemical N-sulfonyl iminophosphoranes from readily available phosphines sulfonamides is reported. This method features low amounts supporting electrolytes, inexpensive electrode materials, a simple galvanostatic setup, high conversion rates. The broad applicability could be demonstrated by synthesizing 20 examples yields up to 90%, having diverse functional groups including chiral moieties biologically relevant species. Furthermore, electrolysis was performed on g scale run repetitive mode recycling the electrolyte, which illustrates suitability for large-scale production. A reaction mechanism involving mediation iodide-based electrolyte proposed, completely agreeing with all results.

Language: Английский

Citations

3
Cu(II)-Catalyzed Aerobic Synthesis of Sulfinamidines from Sulfenamides DOI Creative Commons
Xunbo Lu, Guoling Huang,

Jianlin Ye

et al.

Published: April 19, 2023

Inhere, the first instance of copper-catalyzed oxidative amination sulfenamides for synthesis sulfinamidines was documented. Employing air as terminal oxidant, a variety secondary and primary amines can be effectively transformed into their target products. This reaction boasts excellent chemoselectivity, mild conditions, straightforward operation, broad substrate compatibility, which has significant implications fields pharmaceuticals organic synthesis.

Language: Английский

Citations

5
Electrochemical Synthesis of Isoxazoles and Isoxazolines via Anodic Oxidation of Oximes DOI Creative Commons
Silja Hofmann, J. Winter, Tobias Prenzel

et al.

ChemElectroChem, Journal Year: 2023, Volume and Issue: 10(22)

Published: Oct. 31, 2023

Abstract Isoxazol(in)es are widely featured structural motifs in natural products, agrochemicals, and pharmaceuticals. The first intermolecular approach for a direct electrochemical synthesis from readily available aldoximes is reported. Isoxazoles isoxazolines were obtained yields up to 81 %. carried out an undivided cell as the simplest set‐up requires only use of electric current traceless oxidizing agent. application inexpensive electrode materials combination with recyclable supporting electrolytes solvents paves path translation presented reaction onto preparative scale. This underlined by successful scale‐up multi‐gram runs.

Language: Английский

Citations

5
Progress in S–X Bond Formation by Halogen-Mediated Electrochemical Reactions DOI
Qingwen Gui, Juan Du,

Ya-Long Du

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2799 - 2816

Published: May 19, 2023

Abstract Sulfur-containing compounds are very common and important heteroatom skeletons widely found in natural products, pharmaceuticals bioactive compounds. Moreover, the development of synthetic routes to organosulfur has attracted considerable attention due their wide range applications organic chemistry, pharmaceutical industry materials science. As one most powerful, green eco-friendly research areas, electrosynthesis, contrast conventional synthesis, can avoid use harmful stoichiometric external oxidants or reductants. Importantly, halide salts used as supporting electrolytes redox catalysts indirect electrosynthesis limitations imposed by high overpotentials direct electrosynthesis. In recent years, significant progress been made on halogen-mediated this review, scope, mechanisms electrochemical transformations sulfur-containing presented discussed. 1 Introduction 2 S–C Bond Formation 2.1 Organic Thiocyanates 2.2 Sulfonyl Compounds 2.3 Other Sulfides 3 S–X (X = N, O, S, P) Bonds 4 Conclusion Outlook

Language: Английский

Citations

4