ArticleChemical science2017
Metal-free C-H alkylation of heteroarenes with alkyltrifluoroborates: a general protocol for 1°, 2° and 3° alkylation.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.
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Who cites it
41 citing papers in PubMed.
- A unified strategy for α-alkoxyalkyl radical generationOrganic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Late-Stage Heteroarene Alkylation via Minisci Reaction with Gaseous Alkanes Enabled by Hydrogen Atom Transfer in Flow.ACS central science · 2025Article
- The Golden Age of Thermally Activated Delayed Fluorescence Materials: Design and Exploitation.Chemical reviews · 2024Review
- Parallel Minisci Reaction ofACS organic & inorganic Au · 2024Article
- Late-stage guanine C8-H alkylation of nucleosides, nucleotides, and oligonucleotides via photo-mediated Minisci reaction.Nature communications · 2024Article
- Late-Stage C-H Functionalization of Azines.Chemical reviews · 2023Review
- Photoredox catalysis harvesting multiple photon or electrochemical energies.Beilstein journal of organic chemistry · 2023Review
- Temperature- and pH-Responsive Polymeric Photocatalysts for Enhanced Control and Recovery.Angewandte Chemie (International ed. in English) · 2022Review
- Radical generation enabled by photoinduced N-O bond fragmentation.Chemical science · 2022Article
- The Impact of Boron Hybridisation on Photocatalytic Processes.Angewandte Chemie (International ed. in English) · 2022Review
- Exploiting the spNature chemistry · 2022Article
- Aliphatic C-H Functionalization Using PyridineACS catalysis · 2022Article
- Modular synthesis of α-arylated carboxylic acids, esters and amidesChemical science · 2022Article
- General electrochemical Minisci alkylation ofChemical science · 2022Article
- Photocatalytic C(spChemical science · 2022Review
- Photo-redox catalyzed dehydrazinative acylation of N-heterocyclesRSC advances · 2021Article
- Pyridylphosphonium salts as alternatives to cyanopyridines in radical-radical coupling reactions.Chemical science · 2021Article
- A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes.Journal of the American Chemical Society · 2021Article
- Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophilesChemical science · 2021Article
- Oxidative Three-Component Carboamination of Vinylarenes with Alkylboronic Acids.ACS catalysis · 2021Article
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3 authors.
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Abstract
A photoredox-catalyzed C-H functionalization of heteroarenes using a variety of primary, secondary, and tertiary alkyltrifluoroborates is reported. Using Fukuzumi's organophotocatalyst and a mild oxidant, conditions amenable for functionalizing complex heteroaromatics are described, providing a valuable tool for late-stage derivatization. The reported method addresses the three major limitations of previously reported photoredox-mediated Minisci reactions: (1) use of superstoichiometric amounts of a radical precursor, (2) capricious regioselectivity, and (3) incorporation of expensive photocatalysts. Additionally, a number of unprecedented, complex alkyl radicals are used, thereby increasing the chemical space accessible to Minisci chemistry. To showcase the application in late-stage functionalization, quinine and camptothecin analogues were synthesized. Finally, NMR studies were conducted to provide a rationalization for the heteroaryl activation that permits the use of a single equivalent of radical precursor and also leads to enhanced regioselectivity. Thus, by
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