Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines DOI
Martin Klein, Siegfried R. Waldvogel

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(43), P. 23197 - 23201

Published: Aug. 19, 2021

A novel and very simple to perform electrochemical approach for the synthesis of several N-cyanosulfilimines in good excellent yields was established. This method provides access biologically relevant sulfoximines by consecutive oxidation using electro-generated periodate. route can be easily scaled-up gram quantities. The S,N coupling is carried out at an inexpensive carbon anode direct sulfide. Therefore, designed process atom economic represents a new "green route" sulfilimines sulfoximines.

Language: Английский

LABS: Laboratory Automation and Batch Scheduling – A Modular Open Source Python Program for the Control of Automated Electrochemical Synthesis with a Web Interface DOI Creative Commons
Maximilian M. Hielscher, Maurice Dörr, Johannes Schneider

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(14)

Published: June 3, 2023

With LABS, an open source Python-based lab software is established that enables users to orchestrate automated synthesis setups. The consists of a user-friendly interface for data input and system monitoring. A flexible backend architecture the integration multiple devices. allows easily modify experimental parameters or routines switch between different Compared previously published projects, we aim provide more widely applicable customizable automation any setup. usefulness this tool was demonstrated in oxidative coupling 2,4-dimethyl-phenol corresponding 2,2'-biphenol. In context, suitable electrolysis flow were optimized by way design experiments.

Language: Английский

Citations

12

Choice of the Right Supporting Electrolyte in Electrochemical Reductions: A Principal Component Analysis DOI
Florian Mast, Maximilian M. Hielscher, Tom Wirtanen

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(22), P. 15119 - 15129

Published: May 24, 2024

We present an analysis of a set molecular, electrical, and electronic properties for large number the cations quaternary ammonium salts usually employed as supporting electrolytes in cathodic reduction reactions. The goal study is to define measure quality electrolyte terms yield reaction considered. performed principal component using normalized values order lower relevant coordinates find that integral variance 13 can well be represented by three components. electrochemical hydrodimerization acrylonitrile employing different was determined series experiments. found only very weak correlation between but strong most important component. Very similar results are obtained two further existing systematic experimental studies impact on reductions. For all example reactions, supervised regression components variables yields excellent coefficients determination. comparison, we also applied our methodology sets purely structure-based features cheminformatics almost quality. therefore conjecture combination with small experiments used predict given basis electrolyte.

Language: Английский

Citations

4

Energy-, time-, and labor-saving synthesis of α-ketiminophosphonates: machine-learning-assisted simultaneous multiparameter screening for electrochemical oxidation DOI
Masaru Kondo,

Akimasa Sugizaki,

Md. Imrul Khalid

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(16), P. 5825 - 5831

Published: Jan. 1, 2021

A highly efficient synthesis of α-ketiminophosphonates has been established for the electrochemical oxidation α-amino phosphonates with utilization machine-learning-assisted simultaneous multiparameter screening.

Language: Английский

Citations

25

Multicomponent Electrosynthesis of Enaminyl Sulfonates Starting from Alkylamines, SO2, and Alcohols DOI Creative Commons

Florian A. Breitschaft,

Alicia L. Saak,

Christian Krumbiegel

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 27, 2025

An electrochemical one-pot synthesis of enaminyl sulfonate esters was established, featuring a quasidivided cell under constant current conditions. The multicomponent reaction utilizes simple and readily available alkylamines an easy-to-use stock solution SO2 alcohols. Omission additional supporting electrolyte through in-situ-generated monoalkylsulfite facilitates the downstream processing. A diverse scope with more than 28 examples yields up to 85% as well 20-fold scale-up prove feasibility this novel protocol.

Language: Английский

Citations

0

Reaction development: a student's checklist DOI
Jasper L. Tyler, Dirk Trauner, Frank Glorius

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

So you've discovered a reaction. This review discusses the key areas involved in developing new reactions and provides handy checklist guide to help maximise potential of your novel transformation.

Language: Английский

Citations

0

Electrochemical Decarboxylative Oxidation of Carboxylic Acid Mixtures on Boron Doped Diamond Electrodes DOI
Talal Ashraf, Bastian Mei, Guido Mul

et al.

Electrochimica Acta, Journal Year: 2025, Volume and Issue: 522, P. 145826 - 145826

Published: Feb. 13, 2025

Language: Английский

Citations

0

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

Nitro Substrates in Reductive Electrosynthesis: A Review DOI Creative Commons
Sebastián O. Simonetti, Sebastian B. Beil, Siegfried R. Waldvogel

et al.

ACS electrochemistry., Journal Year: 2025, Volume and Issue: unknown

Published: May 6, 2025

Language: Английский

Citations

0

Optimization Strategies for the Anodic Phenol‐Arene Cross‐Coupling Reaction DOI Creative Commons
Maximilian M. Hielscher, Elisabeth K. Oehl,

Barbara Gleede

et al.

ChemElectroChem, Journal Year: 2021, Volume and Issue: 8(20), P. 3904 - 3910

Published: Sept. 28, 2021

Abstract Dehydrogenative phenol‐arene cross‐coupling by direct anodic oxidation is a promising alternative to reductive cross‐coupling, especially for construction of smaller molecules. The reaction pathway via phenoxyl radicals allows unusual regioselectivity. Nevertheless, the numerous electrolysis parameters pose challenge optimization, as they determine yield and selectivity reaction. Using design experiments, we present optimization strategies two example reactions improve space‐time yield. In particular, coupling with 2,6‐dimethoxyphenol (syringol) were found be very robust in at high current densities up 150 mA/cm 2 . Cyclic voltammetry was used classify combinations phenols arenes, on basis which various clusters optimized. Based this classification, biaryls synthesized isolated yields 85 %.

Language: Английский

Citations

23

High-Throughput Experimentation for Electrochemistry DOI
Jonas Rein, Song Lin, Dipannita Kalyani

et al.

ACS symposium series, Journal Year: 2022, Volume and Issue: unknown, P. 167 - 187

Published: Nov. 15, 2022

ADVERTISEMENT RETURN TO BOOKPREVChapterNEXTHigh-Throughput Experimentation for ElectrochemistryJonas ReinJonas Rein Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United StatesMore by Jonas Rein, Song Lin*Song Lin States*Email: [email protected]More Lin, Dipannita Kalyani*Dipannita Kalyani Discovery Chemistry, Merck & Co., Inc., Kenilworth, Jersey 07033, Kalyani, Dan Lehnherr*Dan Lehnherr Process Research Development, Rahway, 07065, LehnherrDOI: 10.1021/bk-2022-1419.ch010Publication Date (Web):November 15, 2022Publication History Published online15 November 2022RIGHTS PERMISSIONSThe Power High-Throughput Experimentation: General Topics Enabling Technologies Synthesis Catalysis (Volume 1)Chapter 10pp 167-187ACS Symposium SeriesVol. 1419ISBN13: 9780841297579eISBN: 9780841297562 Copyright © 2022 American SocietyChapter Views171Citations-LEARN ABOUT THESE METRICSChapter Views are the COUNTER-compliant sum full text article downloads since 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated to reflect usage leading up last few days.Citations number other articles citing this article, calculated Crossref daily. Find more information about citation counts. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InReddit Read OnlinePDF (6 MB) SUBJECTS:Electrodes,Electrolysis,Electrosynthesis,Materials,Redox reactions Get e-Alerts

Language: Английский

Citations

16