High-Throughput Experimentation for Electrochemistry

Rein, Jonas; Lin, Song; Kalyani, Dipannita; Lehnherr, Dan

doi:10.1021/bk-2022-1419.ch010

Cited by 12 publications

(13 citation statements)

References 69 publications

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“…The development of an electrosynthetic reaction requires tuning of common reaction parameters, such as catalyst, additive, concentration, and temperature, as well as parameters specific to electrochemistry, which are discussed in the following paragraphs. 42 Overall, although operating an electrochemical reaction may initially appear to be labor intensive to non-specialists, it presents several attractive advantages that may prove ultimately beneficial for specific synthetic applications (as discussed in detail in Section 3 through various case studies).…”

Section: Components Of An Electrochemical Reactionmentioning

confidence: 99%

A tutorial on asymmetric electrocatalysis

Rein,

Zacate,

Mao

et al. 2023

Chem. Soc. Rev.

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Section: Components Of An Electrochemical Reactionmentioning

confidence: 99%

A tutorial on asymmetric electrocatalysis

Rein,

Zacate,

Mao

et al. 2023

Chem. Soc. Rev.

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“…Given the multi-variable optimization problem, we turned to high throughput experimentation to address this challenge. Using the recently reported 36 and commercialized 37 HTe -Chem reactor 38 we explored both electrolyte and electrode variables using 4:1 (v/v) NMP/MeOH as the solvent system. The use of Me4NOAc as the electrolyte in combination with platinum cathode and graphite anode provided the highest yield of iminophosphorane 1.…”

Section: Scheme 1 (A) Electrosynthesis Of Iminophosphoranes From Phos...mentioning

confidence: 99%

Electrosynthesis of Iminophosphoranes: Accessing P(V) Ligands from P(III) Phosphines

Mdluli

Lehnherr

Lam

et al. 2023

Preprint

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Iminophosphorane P(V) compounds are accessed via electrochemical oxidation of commercially available P(III) ligands, including mono-, di- and tri-dentate phosphines as well as chiral phosphines. The reaction uses inexpensive bis(trimethylsilyl)carbodiimide as an efficient and safe aminating reagent. DFT calculations, cyclic voltammetry, and NMR spectroscopic studies provide insight into the reaction mechanism. The proposed mechanism based on the data reveals a special case of sequential paired electrolysis, namely a domino electrolysis process in which intermediates generated at the cathode are subsequently oxidized at the anode, followed by an additional convergent paired electrolysis process. DFT calculations of the frontier orbitals of the iminophosphorane are compared to those of the analogous P(III) phosphines and P(V) phosphine oxides. This reveals that N-cyano-iminophosphoranes have both a higher HOMO and lower LUMO than their analogous phosphine oxide, rendering them suitable for both sigma-donating and pi-back-bonding.

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“…28 Considering the exciting progress of utilizing AI for synthetic chemistry and HTE, it is believed that extensive implementation of AI to facilitate the development of electrosynthesis will emerge soon. 35 The following introduces a few existing data-driven approaches for electrochemical screening.…”

Section: Template For Synthesis Thiemementioning

confidence: 99%

“…There have been several seminal reviews available covering various aspects of high-throughput experimentation (HTE) for organic electrosynthesis. 17,[33][34][35] The aim of this short review is to describe recent advances in the enabling screening technology for electrosynthesis, including electrocatalysts screening, screening device miniaturization, electroanalytical methods, artificial intelligence, and screening system integration. The discussed contents cover some topics in HTE electrochemistry for areas other than synthetic chemistry, hoping to spark some inspirations for readers to use interdisciplinary techniques to solve challenges in synthetic electrochemistry.…”

Section: Introductionmentioning

confidence: 99%

Accelerated Electrosynthesis Development Enabled by High-Throughput Experimentation

Chen

2023

Synthesis

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Electrochemical synthesis has recently emerged as an environmentally benign method for synthesizing value-added fine chemicals. Its unique reactivity has attracted significant interests of synthetic chemists to develop new redox chemistries. However, compared to conventional chemistry, the increased complexity caused by electrode materials, supporting electrolytes, and setup configurations create obstacles for efficient reaction discovery and optimization. The recent increasing adoption of high-throughput experimentation (HTE) in synthetic chemistry significantly expedites the synthesis development. Considering the potential of implementing HTE in electrosynthesis to tackle the challenges of increased parameter space, this short review aims at providing recent advances in the HTE technology for electrosynthesis, including electrocatalysts screening, device miniaturization, electroanalytical methods, artificial intelligence, and system integration. The discussed contents also cover some topics in HTE electrochemistry for areas other than synthetic chemistry, hoping to spark some inspirations for readers to use interdisciplinary techniques to solve challenges in synthetic electrochemistry.

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High-Throughput Experimentation for Electrochemistry

Cited by 12 publications

References 69 publications

A tutorial on asymmetric electrocatalysis

A tutorial on asymmetric electrocatalysis

Electrosynthesis of Iminophosphoranes: Accessing P(V) Ligands from P(III) Phosphines

Accelerated Electrosynthesis Development Enabled by High-Throughput Experimentation

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