ArticleJournal of the American Chemical Society2020
Enantioselective Diarylcarbene Insertion into Si-H Bonds Induced by Electronic Properties of the Carbenes.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Enantioconvergent access to 1,1-diarylmethine silanes and germanes through nickel/photoredox-catalyzed cross-electrophile coupling.Chemical science · 2026Article
- Superacid counteranion as flexible-coordinating ligand for asymmetric organo-bismuth catalysis.Nature communications · 2025Article
- Asymmetric Migratory Tsuji-Wacker Oxidation Enables the Enantioselective Synthesis of Hetero- and Isosteric Diarylmethanes.Journal of the American Chemical Society · 2024Article
- Direct synthesis of α-functionalized amides via heteroatom-hydrogen insertion reactions using amide-sulfoxonium ylides.Nature communications · 2024Article
- DigiChemTree enables programmable light-induced carbene generation for on demand chemical synthesis.Communications chemistry · 2024Article
- DJournal of the American Chemical Society · 2024Article
- Enantioselective and Regiodivergent Synthesis of Propargyl- and Allenylsilanes through Catalytic Propargylic C-H Deprotonation.Angewandte Chemie (International ed. in English) · 2024Article
- Enantioselective Synthesis of Triarylmethanes via Intermolecular C-H Functionalization of Cyclohexadienes with Diaryldiazomethanes.Organic letters · 2023Article
- Organocatalytic discrimination of non-directing aryl and heteroaryl groups: enantioselective synthesis of bioactive indole-containing triarylmethanes.Chemical science · 2022Article
- Proton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Dirhodium(ii)-catalysed cycloisomerization of azaenyne: rapid assembly of centrally and axially chiral isoindazole frameworks.Chemical science · 2021Article
- Photochemical Carbene Transfer Reactions of Aryl/Aryl Diazoalkanes-Experiment and Theory*.Angewandte Chemie (International ed. in English) · 2021Article
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8 authors.
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Abstract
Catalytic enantioselection usually depends on differences in steric interactions between prochiral substrates and a chiral catalyst. We have discovered a carbene Si-H insertion in which the enantioselectivity depends primarily on the electronic characteristics of the carbene substrate, and the log(er) values are linearly related to Hammett parameters. A new class of chiral tetraphosphate dirhodium catalysts was developed; it shows excellent activity and enantioselectivity for the insertion of diarylcarbenes into the Si-H bond of silanes. Computational and mechanistic studies show how the electronic differences between the two aryls of the carbene lead to differences in energies of the diastereomeric transition states. This study provides a new strategy for asymmetric catalysis exploiting the electronic properties of the substrates.
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