LABS: Laboratory Automation and Batch Scheduling - A Modular Open Source Python Program for the Control of Automated Electrochemical Synthesis with a Web Interface.

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

Electrochemical C-H Functionalization of (Hetero)Arenes-Optimized by DoE.

A novel approach towards the activation of different arenes and purines including caffeine and theophylline is presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron-doped diamond (BDD) electrodes. Good yields up to 59 % were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized using Design of Experiment (DoE) techniques giving a detailed insight to the significance of the reaction parameters. The mechanism was investigated by cyclic voltammetry (CV). Subsequent transition metal-catalyzed as well as metal-free functionalization led to interesting motifs in excellent yields up to 94 %.

Synthesis of Highly Functionalized N,N-Diarylamides by an Anodic C,N-Coupling Reaction.

We report an innovative, sustainable and straightforward protocol for the synthesis of N,N-diarylamides equipped with nonprotected hydroxyl groups by using electrosynthesis. The concept allows the application of various substrates furnishing diarylamides with yields up to 57 % within a single and direct electrolytic protocol. The method is thereby easy to conduct in an undivided cell with constant current conditions offering a versatile and short-cut alternative to conventional pathways.

Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Benzofurans leading to a Furan Metathesis.

Heterobiaryls consisting of a phenol and a benzofuran motif are of significant importance for pharmaceutical applications. An attractive sustainable, metal- and reagent-free, electrosynthetic, and highly efficient method, that allows access to (2-hydroxyphenyl)benzofurans is presented. Upon the electrochemical dehydrogenative C-C cross-coupling reaction, a metathesis of the benzo moiety at the benzofuran occurs. This gives rise to a substitution pattern at the hydroxyphenyl moiety which would not be compatible by a direct coupling process. The single-step protocol is easy to conduct in an undivided electrolysis cell, therefore scalable, and inherently safe.