Selective electrochemical reductive amination of benzaldehyde at heterogeneous metal surfaces

Schiffer, Zachary J.; Chung, Minju; Steinberg, Katherine; Manthiram, Karthish

doi:10.1016/j.checat.2022.100500

Cited by 11 publications

(13 citation statements)

References 77 publications

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“…The Mosquito/1536-well MTP platform pioneered by Merck Research Laboratories is prevalently reported in the literature for nanoscale optimization. Although this approach has limitations related to the breadth of chemical reaction types that can be performed in 1536-well MTPs (Table ), ultraHTE has been successfully employed on multiple occasions for the multiparameter optimization of a variety of different reaction types from the medicinal chemistry toolbox. ,− These reactions include Suzuki cross-couplings, reductive aminations, N -alkylations, nucleophilic aromatic substitutions (S N Ar), etc., as well as transition-metal catalyzed couplings on pharmaceutically relevant molecules such as the Pd-catalyzed Buchwald–Hartwig amination, metallophotoredox C–N and C–O bond formations, and C–H functionalizations to furnish C(sp 2 )–C(sp 3 ) bonds (Table ).…”

Section: Data-driven Optimizationmentioning

confidence: 99%

A Brief Introduction to Chemical Reaction Optimization

et al. 2023

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From the start of a synthetic chemist’s training, experiments are conducted based on recipes from textbooks and manuscripts that achieve clean reaction outcomes, allowing the scientist to develop practical skills and some chemical intuition. This procedure is often kept long into a researcher’s career, as new recipes are developed based on similar reaction protocols, and intuition-guided deviations are conducted through learning from failed experiments. However, when attempting to understand chemical systems of interest, it has been shown that model-based, algorithm-based, and miniaturized high-throughput techniques outperform human chemical intuition and achieve reaction optimization in a much more time- and material-efficient manner; this is covered in detail in this paper. As many synthetic chemists are not exposed to these techniques in undergraduate teaching, this leads to a disproportionate number of scientists that wish to optimize their reactions but are unable to use these methodologies or are simply unaware of their existence. This review highlights the basics, and the cutting-edge, of modern chemical reaction optimization as well as its relation to process scale-up and can thereby serve as a reference for inspired scientists for each of these techniques, detailing several of their respective applications.

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Section: Data-driven Optimizationmentioning

confidence: 99%

A Brief Introduction to Chemical Reaction Optimization

et al. 2023

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“…For example, reductive amination to produce amines from ammonia and alcohols or aldehydes is prominent in biomass upgrading, but not for wastewater despite numerous ammonia-rich wastewater feedstocks. 162,163 Synthesizing higher molecular weight molecules in the wastewater environment can also minimize needs for dedicated separation steps of reaction intermediates 94 and enable facile separation processes like size exclusion. The concept of biomimicry also applies to selective electrochemical separations.…”

Section: Subsection 2c: Interfacing Selective Materials With Electroc...mentioning

confidence: 99%

Electrochemical wastewater refining: a vision for circular chemical manufacturing

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Guo

et al. 2023

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Wastewater is an underleveraged resource; it contains pollutants that can be transformed into valuable high-purity products. Innovations in chemistry and chemical engineering will play critical roles in valorizing wastewater to remediate environmental pollution, provide equitable access to chemical resources and services, and secure critical materials from diminishing feedstock availability. This perspective envisions electrochemical wastewater refining—the use of electrochemical processes to tune and recover specific products from wastewaters—as the necessary framework to accelerate wastewater-based electrochemistry to widespread practice. We define and prescribe a use-informed approach that simultaneously serves specific wastewater-pollutant-product triads and uncover mechanistic understanding generalizable to broad use cases. We use this approach to evaluate research needs in specific case studies of electrocatalysis, stoichiometric electrochemical conversions, and electrochemical separations. Finally, we provide rationale and guidance for intentionally expanding the electrochemical wastewater refining product portfolio. Wastewater refining will require a coordinated effort from multiple expertise areas to meet the urgent need of extracting maximal value from complex, variable, diverse, and abundant wastewater resources.

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“…Palkovits group 10 studied the effects of different electrochemical variables on the yield of ERA. Recently, Huang group 11 and Manthiram group 12 have conducted several experiments and computation studies to investigate ERA pathways. While ERA is considered as a fairly straightforward reaction that requires two e − /H + transfers, the origin of hydrogen atom sources and reaction intermediates is not fully revealed yet.…”

mentioning

confidence: 99%

“…In this regard, several researchers have studied electrochemical reductive amination for various substrate scopes. [8][9][10][11][12][13][14][15] Choi group 8 and Yan group 9 reported electrode engineering techniques for biomass upconversion. Palkovits group 10 studied the effects of different electrochemical variables on the yield of ERA.…”

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confidence: 99%