ArticleJournal of the American Chemical Society2021
Electrochemical Nozaki-Hiyama-Kishi Coupling: Scope, Applications, and Mechanism.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
31 citing papers in PubMed.
- Photoinduced cobalt-catalyzed enantioconvergent synthesis of 1,3-diamines via aziridine ring-opening addition.Science advances · 2026Article
- Chemo-, Diastereo-, and Enantioselective Radical Cyclization of Enals to Access Cyclopentanols Bearing an α-Quaternary Center.Angewandte Chemie (International ed. in English) · 2026Article
- Enantioselective Vinyl Radical Addition to Aldehydes via Dual Chromium Catalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Review
- Recent Advances in the High-Value Conversion of Alkenes Induced by Electrochemistry.Molecules (Basel, Switzerland) · 2026Review
- Advanced Electrochemical C-C Bond Formation Using a Michael-Type Nozaki-Hiyama-Kishi (NHK) Reaction.ACS omega · 2025Article
- Catalytic 1,2-Migratory Insertion in a Bismuth Redox Platform: Reductive Arylation of Aldehydes.Angewandte Chemie (International ed. in English) · 2025Article
- Unlocking Chromium Decarboxylative Ligand-to-Metal Charge Transfer: Efficient and Redox-Neutral Allylation of Aldehydes Using Carboxylic Acids.Journal of the American Chemical Society · 2025Article
- Cathodic tandem alkylation/dearomatization of heterocycles enabled by Al-facilitated carbonyl deoxygenation.Nature communications · 2025Article
- Electrochemical Enantioselective Nickel-Catalyzed Cross-Coupling of Aldehydes with Aryl Iodides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Electrochemically Driven Nickel-Catalyzed Enantioselective Hydro-Arylation/Alkenylation of Enones.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Electrocatalytic Asymmetric Nozaki-Hiyama-Kishi Decarboxylative Coupling: Scope, Applications, and Mechanism.Journal of the American Chemical Society · 2024Article
- Metal-free photocatalytic cross-electrophile coupling enables C1 homologation and alkylation of carboxylic acids with aldehydes.Nature communications · 2024Article
- Interfacial Tuning of Electrocatalytic Ag Surfaces for Fragment-Based Electrophile Coupling.Nature catalysis · 2024Article
- A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis.Beilstein journal of organic chemistry · 2024Review
- Enabling Al sacrificial anodes in tetrahydrofuran electrolytes for reductive electrosynthesis.Chemical science · 2023Article
- Electrochemical Late-Stage Functionalization.Chemical reviews · 2023Review
- First Reusable Catalyst for the Reductive Coupling Reaction of Organohalides with Aldehydes.ACS omega · 2023Article
- Electronic Structures of Nickel(II)-Bis(indanyloxazoline)-dihalide Catalysts: Understanding Ligand Field Contributions That Promote C(spInorganic chemistry · 2023Article
- Deep Electroreductive Chemistry: Harnessing Carbon- and Silicon-based Reactive Intermediates in Organic Synthesis.ACS catalysis · 2023Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
9 authors.
Funding
Abstract
One of the most oft-employed methods for C-C bond formation involving the coupling of vinyl-halides with aldehydes catalyzed by Ni and Cr (Nozaki-Hiyama-Kishi, NHK) has been rendered more practical using an electroreductive manifold. Although early studies pointed to the feasibility of such a process, those precedents were never applied by others due to cumbersome setups and limited scope. Here we show that a carefully optimized electroreductive procedure can enable a more sustainable approach to NHK, even in an asymmetric fashion on highly complex medicinally relevant systems. The e-NHK can even enable non-canonical substrate classes, such as redox-active esters, to participate with low loadings of Cr when conventional chemical techniques fail. A combination of detailed kinetics, cyclic voltammetry, and in situ UV-vis spectroelectrochemistry of these processes illuminates the subtle features of this mechanistically intricate process.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.