ArticleJournal of the American Chemical Society2023
Efficient Synthesis of α-Haloboronic Esters via Cu-Catalyzed Atom Transfer Radical Addition.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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Who cites it
9 citing papers in PubMed, 19 citations in OpenAlex.
- Regioselective multicomponent synthesis of α-boryl ureas: discovery of a potent main protease inhibitor.Organic & biomolecular chemistry · 2026Article
- Chloroalkylation of Unactivated Alkenes via a Cobalt-Mediated Radical Ligand Transfer (RLT) Photoredox Catalysis Platform.JACS Au · 2025Article
- Functional Group Transposition Enabled by Palladium and Photo Dual Catalysis.Journal of the American Chemical Society · 2025Article
- Palladium-Catalyzed Aerobic Alkene Arylboration: Coupling Aryl Boronic Acids, Alkenes, and Bis(pinacol)diboron.ACS catalysis · 2025Article
- Kharasch-Type Haloalkylation of Alkenes by Photoinduced Copper Catalysis.Journal of the American Chemical Society · 2025Article
- A General Platform for Copper-Catalyzed Atom Transfer Radical Addition with Electron-Deficient Olefins.Organic letters · 2025Article
- BrCFNature communications · 2025Article
- Cu-Catalyzed Three-Component Alkene Carboamination: Mechanistic Insights and Rational Design to Overcome Limitations.Journal of the American Chemical Society · 2024Article
- Mechanochemical Synthesis of α-halo Alkylboronic Esters.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
The synthesis of α-haloboronic esters via atom transfer radical addition (ATRA) is constrained due to its limited range of compatible substrates or the need to manipulate the olefin coupling partners. Herein, we present a novel approach for their synthesis via Cu-catalyzed ATRA to vinyl boronic esters. The catalyst is proposed to mediate a traditionally inefficient halogen atom transfer of the α-boryl radical intermediate, thus significantly expanding the range of participating substrates relative to established methods. The forty-eight examples illustrate that a wide range of radical precursors, including primary, secondary, and tertiary alkyl halides, readily add across both unsubstituted and α-substituted vinyl pinacol boronic esters. Further, a one-pot, two-step protocol is presented for direct access to an array of α-functionalized products. Finally, the synthetic utility of this methodology is demonstrated in the synthesis of an ixazomib analogue.
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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.