ArticleChemical science2019
Enantioselective photoredox dehalogenative protonation.
Article in Chemical science, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Dicyanopyrazine: 10th Anniversary in Photoredox Catalysis.Chemical record (New York, N.Y.) · 2025Article
- Asymmetric Synthesis of α-Chloroamides via Photoenzymatic Hydroalkylation of Olefins.Journal of the American Chemical Society · 2024Article
- Radical Cross Coupling and Enantioselective Protonation through Asymmetric Photoredox Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Catalytic Enantioselective Protonation of Gold Enolates Enabled by Cooperative Gold(I) Catalysis.Journal of the American Chemical Society · 2024Article
- Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Syntheses of new chiral chimeric photo-organocatalysts.RSC advances · 2021Article
- Exploiting attractive non-covalent interactions for the enantioselective catalysis of reactions involving radical intermediates.Nature chemistry · 2020Review
- Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions.Chemical science · 2020Article
- Recent developments in enantioselective photocatalysis.Beilstein journal of organic chemistry · 2020Review
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report an enantioselective photoredox dehalogenative protonation as a new type of asymmetric protonation. As a paradigm, with a cooperative catalytic system consisting of a chiral H-bonding catalyst and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer that is irradiated with visible light, a range of cyclic and acyclic ketones with labile chiral secondary C-F, C-Cl and C-Br bonds at the α-position were obtained in high yields with good to excellent enantioselectivities (up to >99% ee) by using a secondary amine as the terminal reductant. Given the ready accessibility of halides, the success of this work should provide inspiration for constructing diverse chiral α-tertiary carbonyls and their variants.
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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.