ArticleAngewandte Chemie (International ed. in English)2020
Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 45 citations in OpenAlex.
- Ambient synthesis of single-atom catalysts on catalytically active cells for chemoenzymatic cascades.Nature communications · 2026Article
- Rieske Oxygenase-Catalyzed Biotransformations in Recombinant Cupriavidus necator Fueled by Formate Oxidation.Chembiochem : a European journal of chemical biology · 2025Article
- Copper(II)-catalyzed selective reduction of chalcones using phenylsilane.Tetrahedron letters · 2025Article
- Catalysis in the Excited State: Bringing Innate Transition Metal Photochemistry into Play.ACS catalysis · 2025Review
- Mild and Chemoselective Carboxylic Acid Reduction Promoted by Borane Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Controlling Chemoselectivity of Catalytic Hydroboration with Light.Angewandte Chemie (International ed. in English) · 2022Article
- Visible-Light-Induced Homolysis of Earth-Abundant Metal-Substrate Complexes: A Complementary Activation Strategy in Photoredox Catalysis.Angewandte Chemie (International ed. in English) · 2021Review
- Using Light to Modify the Selectivity of Transition Metal Catalysed Transformations.Angewandte Chemie (International ed. in English) · 2021Review
- Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride.Journal of the American Chemical Society · 2021Article
- Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
4 authors at 1 institution in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their "hard" or "soft" character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.
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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.