ArticleNature communications2019
Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Metal-free radical borylations: mechanisms, catalytic strategies, and synthetic applications.Chemical science · 2026Review
- Indigenous LDPE degradation bacteria from plastic dumping soils of Thoothukudi coast: isolation, characterization and degradation efficiency.Archives of microbiology · 2026Article
- Synthesis and Suzuki-Miyaura Cross-Coupling of Alkyl Amine-Boranes. A Boryl Radical-Enabled Strategy.Journal of the American Chemical Society · 2024Article
- Diastereoselective dearomatization of indoles via photocatalytic hydroboration on hydramine-functionalized carbon nitride.Nature communications · 2024Article
- Boryls, their compounds and reactivity: a structure and bonding perspective.Chemical science · 2024Review
- Photocatalytic Boryl Radicals Triggered Sequential B─N/C─N Bond Formation to Assemble Boron-Handled Pyrazoles.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Regioselective Electrophilic Addition to Propargylic B(MIDA)s Enabled by β-Boron Effect.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Selective multifunctionalization ofChemical science · 2023Article
- Atomically Precise Metal Nanoclusters as Single Electron Transferers for Hydroborylation.Precision chemistry · 2023Article
- Photocatalyzed regioselective hydrosilylation for the divergent synthesis of geminal and vicinal borosilanes.Nature communications · 2023Article
- Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades.Nature communications · 2022Article
- Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes.Angewandte Chemie (International ed. in English) · 2021Article
- Electrochemical Hydroboration of Alkynes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones.Angewandte Chemie (International ed. in English) · 2020Article
- Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes.Chemical science · 2020Article
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Authors and funding
8 authors.
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Abstract
Organoboron compounds are highly valuable in synthetic chemistry. In particular, α-borylcarbonyl compounds have shown versatile synthetic applications, owing to fruitful chemistries of both the boryl and carbonyl moieties. However, the synthesis of these molecules still remains tedious and time-consuming. Here we report a straightforward and practical route to synthesize α-borylcarbonyl molecules based on a regioselective radical α-borylation of α,β-unsaturated carbonyl compounds. The reaction features unusual α-regioselectivity and high functional-group compatibility. Further synthetic applications of new α-borylated products were also demonstrated. DFT and kinetic studies implicated that the α-regioselectivity of β-aryl-α,β-unsaturated carbonyl compounds was determined by the thermodynamically more favorable radical α-addition step, whereas the formation of α-addition products from β-alkyl-α,β-unsaturated carbonyl compounds was driven by an energetically favored hydrogen atom transfer step. Given that α,β-unsaturated carbonyl compounds can be easily obtained in abundance and variety, this method enjoys great advantages in diverse and economical synthesis of valuable α-borylcarbonyl molecules.
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