ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey-Seebach Reaction.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Photoredox-Catalyzed Generation of Tertiary Anions from Primary Amines via a Radical Polar Crossover.Angewandte Chemie (International ed. in English) · 2024Article
- Gram-scale photosynthesis of polyfunctionalized dihydro-2-oxypyrroles using 3DPAFIPN as a halogenated dicyanobenzene-based photosensitizer via a consecutive visible-light-induced electron transfer process.Frontiers in chemistry · 2024Article
- Halogenated dicyanobenzene-based photosensitizer (3DPAFIPN) as a thermally activated delayed fluorescence (TADF) used in gram-scale photosynthesis 3,4-dihydropyrimidin-2-(1Frontiers in chemistry · 2024Article
- 3DPAFIPN as a halogenated dicyanobenzene-based photosensitizer catalyzed gram-scale photosynthesis of pyrano[2,3-d]pyrimidine scaffolds.Scientific reports · 2023Article
- The Corey-Seebach Reagent in the 21st Century: A Review.Molecules (Basel, Switzerland) · 2023Review
- Light-Induced Access to Carbazole-1,3-dicarbonitrile: A Thermally Activated Delayed Fluorescent (TADF) Photocatalyst for Cobalt-Mediated Allylations.The Journal of organic chemistry · 2023Article
- Efficient Copper-Catalyzed Highly Stereoselective Synthesis of Unprotected C-Acyl Manno-, Rhamno- and Lyxopyranosides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Visible Light-Mediated, Highly Diastereoselective Epimerization of Lactams from the Most Accessible to the More Stable Stereoisomer.ACS catalysis · 2022Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- A Change from Kinetic to Thermodynamic Control EnablesJournal of the American Chemical Society · 2022Article
- Decatungstate-Mediated C(spAngewandte Chemie (International ed. in English) · 2021Article
- Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(spAngewandte Chemie (International ed. in English) · 2021Article
- Strategies for the Photocatalytic Generation of Carbanion Equivalents for Reductant-Free C-C Bond Formations.Accounts of chemical research · 2021Article
- Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey-Seebach Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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5 authors.
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Abstract
A metal-free generation of carbanion nucleophiles is of prime importance in organic synthesis. Herein we report a photocatalytic approach to the Corey-Seebach reaction. The presented method operates under mild redox-neutral and base-free conditions giving the desired product with high functional group tolerance. The reaction is enabled by the combination of photo- and hydrogen atom transfer (HAT) catalysis. This catalytic merger allows a C-H to carbanion activation by the abstraction of a hydrogen atom followed by radical reduction. The generated nucleophilic intermediate is then capable of adding to carbonyl electrophiles. The obtained dithiane can be easily converted to the valuable α-hydroxy carbonyl in a subsequent step. The proposed reaction mechanism is supported by emission quenching, radical-radical homocoupling and deuterium labeling studies as well as by calculated redox-potentials and bond strengths.
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