ArticleJournal of the American Chemical Society2019
A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 60 papers.
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Who cites it
60 citing papers in PubMed, 233 citations in OpenAlex.
- Adamantyl-BOX Ligand Enabling Stereoselective Synthesis of Axially Chiral Aldehydes Bearing Vicinal Stereogenic Centers.ACS central science · 2026Article
- A Dual Photoredox/Cobalt Catalytic System Enables Markovnikov-Selective Hydroaminoalkylation of Alkenes.Precision chemistry · 2026Article
- Direct Access to Acylboranes via Formal Condensation of Carboxylic Acids with Ligated Boranes.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Ni-Catalyzed Reductive Coupling of Acetals with Anhydrides and Vinyl Triflates via Single-Electron C-O Activation.Organic letters · 2025Article
- Combining biocatalytic and radical retrosynthesis for efficient chemoenzymatic synthesis of natural products.Chemical Society reviews · 2025Review
- 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
- Cyclic Imine-BFSynlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Synthesis of C4-Acyl Glycosides by Cross-Ketonization: The Importance of Precise Temperature Control in Photochemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Stereoselective amino alcohol synthesis via chemoselective electrocatalytic radical cross-couplings.Nature chemistry · 2025Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Photocatalytic Decarboxylative Alkylation of Cyclic Imine-BFJournal of the American Chemical Society · 2024Article
- A decarbonylative approach to alkylnickel intermediates and C(spScience (New York, N.Y.) · 2024Article
- Synthesis of Stereodefined Enones from the Cross-Electrophile Coupling of Activated Acrylic Acids with Alkyl Bromides.Organic letters · 2024Article
- Electrochemical Glycosylation via Halogen-Atom-Transfer forACS catalysis · 2024Article
- Enantioselective Synthesis of α-Chiral Bicyclo[1.1.1]pentanes via Multicomponent Asymmetric Allylic Alkylation.Organic letters · 2024Article
- Electrocatalytic Asymmetric Nozaki-Hiyama-Kishi Decarboxylative Coupling: Scope, Applications, and Mechanism.Journal of the American Chemical Society · 2024Article
- Enantioselective synthesis of chiral BCPs.Organic chemistry frontiers : an international journal of organic chemistry · 2024Review
- Mechanisms for radical reactions initiating fromBeilstein journal of organic chemistry · 2024Article
- Nickel-Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to α-Amino Ketones.Angewandte Chemie (International ed. in English) · 2023Article
Corrections and comments
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Authors and funding
20 authors at 5 institutions in 2 countries.
Funding
Abstract
Historically accessed through two-electron, anionic chemistry, ketones, alcohols, and amines are of foundational importance to the practice of organic synthesis. After placing this work in proper historical context, this Article reports the development, full scope, and a mechanistic picture for a strikingly different way of forging such functional groups. Thus, carboxylic acids, once converted to redox-active esters (RAEs), can be utilized as formally nucleophilic coupling partners with other carboxylic derivatives (to produce ketones), imines (to produce benzylic amines), or aldehydes (to produce alcohols). The reactions are uniformly mild, operationally simple, and, in the case of ketone synthesis, broad in scope (including several applications to the simplification of synthetic problems and to parallel synthesis). Finally, an extensive mechanistic study of the ketone synthesis is performed to trace the elementary steps of the catalytic cycle and provide the end-user with a clear and understandable rationale for the selectivity, role of additives, and underlying driving forces involved.
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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.