A Review of Electrochemical Synthesis and Transformations of Small Organic Molecules: Sulfoximines, Isoxazolines, and Benzimidazoles DOI
Sanjay M. Madurkar, Girdhar Pal Singh, Siddharth Sharma

et al.

Current Green Chemistry, Journal Year: 2024, Volume and Issue: 12(2), P. 85 - 116

Published: Sept. 26, 2024

In the realm of synthetic organic chemistry, environmentally friendly manipulation small molecules has gained prominence. One particularly promising approach is electrochemical synthesis, which offers a green and sustainable alternative to using hazardous toxic redox reagents. By harnessing electric current from renewable sources like sunlight or wind, synthesis emerges as viable replacement for conventional methods. This review article provides comprehensive exploration method, delving into its background applications in synthesizing transforming various molecules, including sulfoximines, isoxazolines, benzimidazoles, more. aims shed light on potential greener more way conducting transformations.

Language: Английский

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
Electrochemical Heterocyclic Ring-Formation Reactions by Making C–N and N–N Bonds DOI
Alexander Sandvoß, J. Winter, Tobias Prenzel

et al.

Topics in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

Citations

1
Biphasic Electrosynthesis of 2-Isoxazol(in)e-3-carboxylates: Reaction Optimization from Milligram to Hectogram Scale DOI Creative Commons
Yuto Nakamura, Martin Linden, J. Winter

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(30), P. 11369 - 11376

Published: July 15, 2024

An electrochemical synthesis of isoxazol(in)e-3-carboxylates in a biphasic system allowing the direct access to technically relevant motifs good yields has been established. The versatility this protocol was demonstrated by >30 highly functionalized and diverse examples. Furthermore, derivative isoxadifen-ethyl synthesized more sustainable approach, avoiding hazardous reagents generation large amounts waste. A nitrile oxide as key intermediate is formed without addition strong bases or oxidizers directly undergoes desired cycloaddition. technical relevance established method underlined hectogram-scale while purifying crude product simple silica filtration. By distillation, nonconverted styrene largely recovered, demonstrating sustainability method.

Language: Английский

Citations

0
In‐Situ Electrolyte for Electrosynthesis: Scalable Anodically‐Enabled One‐Pot Sequence from Aldehyde to Isoxazol(in)es DOI Creative Commons

Abdulaziz A. Al‐Romema,

Honglin Xia,

Karl J. J. Mayrhofer

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(68)

Published: Aug. 27, 2024

Abstract Electrochemical transformations are considered a green alternative to classical redox chemistry as it eliminates the necessity for toxic and waste producing reagents. Typical electrochemical reactions require addition of supporting electrolyte – an ionic compound facilitate reaction medium conductivity. However, this is often accompanied by increase in amount produced waste. Here, we report “ in‐situ ” concept facile, transition‐metal‐free, additive‐free one‐pot preparation isoxazol(in)es, important scaffolds biologically active natural synthetic molecules, from respective aldehydes. The protocol utilizes no halogenated solvents external oxidants, while salt side‐products provide conductivity necessary electrosynthesis. electrolysis performed undivided cell, using state‐of‐the‐art electrodes chlor‐alkali industry dimensionally stable scalable mixed metal oxide anode platinized titanium cathode high durability. cascade transformation comprises condensation aldehyde oxime followed its anodic oxidation subsequent intra‐ and/or intermolecular [3+2] cycloadditions with appropriate dipolarophile. Chemical yields up 97 %, good Faradaic efficiency, scalability, stability observed most substrates broad scope.

Language: Английский

Citations

0
A Review of Electrochemical Synthesis and Transformations of Small Organic Molecules: Sulfoximines, Isoxazolines, and Benzimidazoles DOI
Sanjay M. Madurkar, Girdhar Pal Singh, Siddharth Sharma

et al.

Current Green Chemistry, Journal Year: 2024, Volume and Issue: 12(2), P. 85 - 116

Published: Sept. 26, 2024

In the realm of synthetic organic chemistry, environmentally friendly manipulation small molecules has gained prominence. One particularly promising approach is electrochemical synthesis, which offers a green and sustainable alternative to using hazardous toxic redox reagents. By harnessing electric current from renewable sources like sunlight or wind, synthesis emerges as viable replacement for conventional methods. This review article provides comprehensive exploration method, delving into its background applications in synthesizing transforming various molecules, including sulfoximines, isoxazolines, benzimidazoles, more. aims shed light on potential greener more way conducting transformations.

Language: Английский

Citations

0