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Relevant academic research and scientific papers

A Multifunctional Microfluidic Platform for High-Throughput Experimentation of Electroorganic Chemistry

Electroorganic synthesis is a promising tool to design sustainable transformations and discover new reactivities. However, the added setup complexity caused by electrodes in the system impedes efficient screening of reaction conditions. Herein, we present a microfluidic platform that enables automated high-throughput experimentation (HTE) for electroorganic synthesis at a 15-microliter scale. Two HTE modules are demonstrated: 1) the rapid electrochemical reaction condition screening for a radical–radical cross-coupling reaction on micro-fabricated interdigitated electrodes, and 2) measurements of kinetics for mediated anodic oxidations using the microliter-scale cyclic voltammetry. The presented modular approach could be deployed for a range of other electroorganic chemistry applications beyond the demonstrated functionalities.

Mechanistic Investigations of an α-Aminoarylation Photoredox Reaction

While photoredox catalysis continues to transform modern synthetic chemistry, detailed mechanistic studies involving direct observation of reaction intermediates and rate constants are rare. By use of a combination of steady state photochemical measuremen

Visible-Light-Induced α-Amino C-H Bond Arylation Enabled by Electron Donor-Acceptor Complexes

Enabled by electron donor-acceptor complexes, a novel visible-light-induced α-amino C-H bond arylation protocol, without a photoredox catalyst, has been disclosed. The protocol does not require any transition metal, oxidant, or exclusion of oxygen or moisture. A direct irradiation of the mixture of tertiary amines and benzonitriles with visible light in N,N-diethylethanamide in the presence of Cs2CO3 afforded α-arylated amines in good to excellent yields.

Dye-polyoxometalate coordination polymer as a photo-driven electron pump for photocatalytic radical coupling reactions

To alleviate diffusion-limited photoinduced electron transfer (PET) in solution, a triphenylamine-derived dye and a Keggin polyoxometalate-type electron relay were coupled into a coordination polymer to photoinduce long-lived charge-separation pairs with

Tertiary amine alpha-position arylation method

The invention discloses a tertiary amine alpha-position arylation method, which comprises the following steps of: stirring tertiary amine and a cyanobenzene derivative which are used as raw materials in an organic solvent for a certain time by using inorg

Triarylamine-based porous coordination polymers performing both hydrogen atom transfer and photoredox catalysis for regioselective α-amino C(sp3)-H arylation

Direct functionalization of C(sp3)-H bonds in a predictable, selective and recyclable manner has become a central challenge in modern organic chemistry. Through incorporating different triarylamine-containing ligands into one coordination polymer, we present herein a heterogeneous approach to the combination of hydrogen atom transfer (HAT) and photoredox catalysis for regioselective C-H arylation of benzylamines. The different molecular sizes and coordination modes of the ligands, tricarboxytriphenylamine (H3TCA) and tris(4-(pyridinyl)phenyl)amine (NPy3), in one coordination polymer consolidate the triarylamine (Ar3N) moiety into a special structural intermediate, which enhances the chemical and thermal stability of the polymers and diminishes structural relaxation during the catalytic process. The inherent redox potentials of Ar3N moieties prohibit thein situformed Ar3N˙+to earn an electron from C(sp3)-H nucleophiles, but allow the abstraction of a hydrogen atom from C(sp3)-H nucleophiles, enabling the formation of the C(sp3)˙ radical and the cross-coupling reaction to proceed at the most electron-rich sites with excellent regioselectivity. The new heterogeneous photoredox HAT approach skips several interactions between transient species during the typical synergistic SET/HAT cycles, demonstrating a promising redox-economical and reagent-economical heterogeneous platform that has not been reported for α-amino C-H arylation to form benzylamine derivatives. Control experiments based on monoligand coordination polymers suggested that the mixed-ligand approach improved the photochemical and photophysical properties, providing important insight into rational design and optimization of recyclable photocatalysts for rapid access to complex bioactive molecules and late-stage functionalized pharmaceuticals.

Direct Arylation of α-Amino C(sp3)-H Bonds by Convergent Paired Electrolysis

A metal-free convergent paired electrolysis strategy to synthesize benzylic amines through direct arylation of tertiary amines and benzonitrile derivatives at room temperature has been developed. This TEMPO-mediated electrocatalytic reaction makes full use of both anodic oxidation and cathodic reduction without metals or stoichiometric oxidants, thus showing great potential and advantages for practical synthesis. This convergent paired electrolysis method provides a straightforward and powerful means to activate C?H bonds and realize cross-coupling with cathodically generated species.