ArticleAngewandte Chemie (International ed. in English)2017
Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans.
Article in Angewandte Chemie (International ed. in English), 2017. 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.
- Enabling sulfur-centered nucleophiles in conjunctive coupling: triethylborane-mediated trifluoromethylationChemical science · 2026Article
- Thiophenium Salts as New Oxidant for Redox Polymerization under Mild- and Low-Toxicity Conditions.Molecules (Basel, Switzerland) · 2023Article
- Transition-Metal-Free Oxidative Cross-Coupling of Tetraarylborates to Biaryls Using Organic Oxidants.Angewandte Chemie (International ed. in English) · 2020Article
- Recent Advances in Radical Addition to Alkenylboron Compounds.European journal of organic chemistry · 2020Article
- Catalytic Enantioselective Synthesis of β-Allenyl Boronic Esters by Conjunctive Cross-Coupling with Propargylic Carbonates.ACS catalysis · 2019Article
- Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.Angewandte Chemie (International ed. in English) · 2019Article
- Photoredox-Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition-Polar Cyclization Cascade.Angewandte Chemie (International ed. in English) · 2019Article
- Diastereoselective and Enantioselective Conjunctive Cross-Coupling Enabled by Boron Ligand Design.Journal of the American Chemical Society · 2018Article
- Enantiospecific Three-Component Alkylation of Furan and Indole.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Reactivity of fluorographene is triggered by point defects: beyond the perfect 2D world.Nanoscale · 2018Article
- Synthesis of α-Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes.Angewandte Chemie (International ed. in English) · 2018Article
- Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans.Angewandte Chemie (International ed. in English) · 2017Article
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4 authors.
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Abstract
In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2-lithio furan and non-racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three-component coupling to give the corresponding 2,5-disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2-metallate rearrangement upon single-electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three-component coupling reactions.
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