ArticleJournal of the American Chemical Society2024
Electrocatalytic Asymmetric Nozaki-Hiyama-Kishi Decarboxylative Coupling: Scope, Applications, and Mechanism.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 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
- Cobalt-catalyzed asymmetric three-component reductive addition of alkynes with alkyl halides and imines.Nature communications · 2026Article
- Review
- Enantioconvergent radical addition of racemic alkyl halides to access vicinal stereocentres.Nature chemistry · 2026Article
- Ni-Catalyzed Reductive Coupling of Acetals with Anhydrides and Vinyl Triflates via Single-Electron C-O Activation.Organic letters · 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
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
The first general enantioselective alkyl-Nozaki-Hiyama-Kishi (NHK) coupling reactions are disclosed herein by employing a Cr-electrocatalytic decarboxylative approach. Using easily accessible aliphatic carboxylic acids (via redox-active esters) as alkyl nucleophile synthons, in combination with aldehydes and enabling additives, chiral secondary alcohols are produced in a good yield with high enantioselectivity under mild reductive electrolysis. This reaction, which cannot be mimicked using stoichiometric metal or organic reductants, tolerates a broad range of functional groups and is successfully applied to dramatically simplify the synthesis of multiple medicinally relevant structures and natural products. Mechanistic studies revealed that this asymmetric alkyl e-NHK reaction was enabled by using catalytic tetrakis(dimethylamino)ethylene, which acts as a key reductive mediator to mediate the electroreduction of the Cr
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Registered trials
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