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

Synthesis of Sulfilimines via Selective S–C Bond Formation in Water DOI
Yue Chen, Dongmei Fang,

He-sen Huang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(12), P. 2134 - 2138

Published: March 20, 2023

Sulfilimines are valuable compounds both in organic synthesis and pharmaceuticals. Here we developed a mild simplified method for preparation of sulfilimines via selective S–C bond formation rather than traditional S–N formation. The is attractive useful the following reasons: it uses readily available alkylation reagent such alkyl bromide or iodide, water as solvent, easy to perform, convenient late-stage diversification drugs.

Language: Английский

Citations

44
Light-harvesting microelectronic devices for wireless electrosynthesis DOI
Bartosz Górski, Jonas Rein,

Samantha L. Norris

et al.

Nature, Journal Year: 2025, Volume and Issue: 637(8045), P. 354 - 361

Published: Jan. 8, 2025

Language: Английский

Citations

3
Dual Roles of Supporting Electrolytes in Organic Electrosynthesis DOI Creative Commons

Lilla G. Gombos,

Joachim Nikl,

Siegfried R. Waldvogel

et al.

ChemElectroChem, Journal Year: 2024, Volume and Issue: 11(8)

Published: Jan. 18, 2024

Abstract Synthetic electro‐organic chemistry is advancing to a well‐established methodology in academic research and industry. The simple process control minimizes reagent waste avoids using toxic environmentally unfriendly redox agents, providing feasible sustainable alternative conventional techniques. However, fundamental disadvantage, the necessity of ion‐conductive components within electrolyte. recovery these supporting electrolytes, as well product isolation, pose challenges for work‐up strategies. This review presents following electrochemical protocols featuring material‐ resource‐saving strategy: dual role electrolytes conductivity enabling reagents or meditators. first conclude categorize strategies electrolytes. It may inspire electrochemists advance development optimization synthesis towards more resource‐efficient reaction control.

Language: Английский

Citations

16
E-Dakin reaction: oxidation of hydroxybenzaldehydes to phenols with electrochemically generated peroxodicarbonate as sustainable ex-cell oxidizer DOI Creative Commons
Fiona Sprang, Niclas Schupp, Philipp J. Kohlpaintner

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(10), P. 5862 - 5868

Published: Jan. 1, 2024

Peroxodicarbonate, a sustainable electrochemically generated oxidizer, provides the means to transform abundant hydroxybenzaldehydes into valuable phenols in safe and effective manner.

Language: Английский

Citations

6
Enantioselective Synthesis of Sulfinamidines via Asymmetric Nitrogen Transfer from N−H Oxaziridines to Sulfenamides DOI Creative Commons

Marc Fimm,

Fumito Saito

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(35)

Published: May 15, 2024

Sulfinamidines are promising aza-S

Language: Английский

Citations

6
Highly selective scalable electrosynthesis of 4-hydroxybenzo[e]-1,2,4-thiadiazine-1,1-dioxides DOI Creative Commons
J. Winter, Tobias Prenzel, Tom Wirtanen

et al.

Cell Reports Physical Science, Journal Year: 2024, Volume and Issue: 5(5), P. 101927 - 101927

Published: April 15, 2024

4H-4-Hydroxybenzo[e]-1,2,4-thiadiazine-1,1-dioxides are based on a widely found structural motif for pharmaceutical applications, having an additional unique exocyclic N–O bond that is not accessible by conventional synthetic routes. Electrochemistry offers sustainable tool the direct synthesis of these heterocyclic structures containing this N-hydroxy modification. Here, we report highly selective 4H-4-hydroxybenzo[e]-1,2,4-thiadiazine-1,1-dioxides reduction available nitro arenes in almost quantitative yields. The electro-synthetic protocol applied to more than 40 diverse examples, highlighting versatility method. Furthermore, technical relevance demonstrated two multi-gram-scale syntheses.

Language: Английский

Citations

5
Synthesis of functionalized sulfilimines via iron-catalyzed sulfur alkylation of sulfenamides with diazo compounds DOI

Xianda Wu,

Minghong Chen, Fu‐Sheng He

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(22), P. 9092 - 9096

Published: Jan. 1, 2023

An efficient iron-catalyzed sulfur alkylation of sulfenamides with diazo compounds for the synthesis functionalized sulfilimines is developed under air conditions.

Language: Английский

Citations

12
Electrochemical Hofmann rearrangement at high current densities in a simple flow setup DOI Creative Commons
Darryl Nater,

P. Hendriks,

Siegfried R. Waldvogel

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 554, P. 113823 - 113823

Published: Jan. 16, 2024

A reliable electrochemical version for the Hofmann rearrangement has been established, which can be performed at high current density in simple, commercial flow electrolysis cells. The protocols have optimized towards both aromatic and aliphatic substrates, yielding good to excellent yields across a broad substrate scope. method also easily multi-gram scale.

Language: Английский

Citations

4
Lab-scale flow chemistry? Just do it yourself! DOI

Laura Y. Vázquez-Amaya,

Guglielmo Coppola, Erik V. Van der Eycken

et al.

Journal of Flow Chemistry, Journal Year: 2024, Volume and Issue: 14(1), P. 257 - 279

Published: Feb. 23, 2024

Language: Английский

Citations

4
Peroxodicarbonate – A Renaissance of an Electrochemically Generated Green Oxidizer DOI Creative Commons
Theresa Rücker, Niclas Schupp, Fiona Sprang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(56), P. 7136 - 7147

Published: Jan. 1, 2024

Peroxodicarbonate, accessible from direct anodic conversion of alkali carbonates, has experienced a renaissance in the past two decades. An overview its history, synthesis, characteristics and reactivity is provided.

Language: Английский

Citations

4