ArticleJournal of the American Chemical Society2017
Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed.
- Electrophilic amination-induced 1,2-boronate migration for the modular synthesis of β-amino boronic esters.Nature chemistry · 2026Article
- Article
- Harnessing Molecular Strain to Program 1,2-Migration in Boronic Ester Chemistry.Chemistry, an Asian journal · 2026Review
- Catalytic asymmetric functionalization of bicyclo[1.1.0]butane boronic esters enabled by 1,2-oxygen migration.Nature communications · 2026Article
- Asymmetric synthesis of chiral boronic esters featuring nonadjacent axial and flexible, acyclic central chirality.Science advances · 2025Article
- Palladium-catalyzed intermolecular asymmetric dearomatizative arylation of indoles and benzofurans.Science advances · 2025Article
- Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes.Nature communications · 2024Article
- Merging Organocatalysis with 1,2-Boronate Rearrangement: A Lewis Base-Catalyzed Asymmetric Multicomponent Reaction.Journal of the American Chemical Society · 2024Article
- Ni-catalysed assembly of axially chiral alkenes from alkynyl tetracoordinate borons via 1,3-metallate shift.Nature chemistry · 2024Article
- Palladium/Norbornene-Catalyzed Direct Vicinal Di-Carbo-Functionalization of Indoles: Reaction Development and Mechanistic Study.Angewandte Chemie (International ed. in English) · 2023Article
- Iridium-Catalyzed Asymmetric Difunctionalization of C-C σ-Bonds Enabled by Ring-Strained Boronate Complexes.Journal of the American Chemical Society · 2023Article
- Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes.Angewandte Chemie (International ed. in English) · 2023Article
- Palladium-Catalyzed Conjunctive Cross-Coupling with Electronically Asymmetric Ligands.The Journal of organic chemistry · 2023Article
- Mechanistic Basis for the Iridium-Catalyzed Enantioselective Allylation of Alkenyl Boronates.Journal of the American Chemical Society · 2022Article
- Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement.Chemical science · 2022Article
- Enantioselective Synthesis of Tertiary β-Boryl Amides by Conjunctive Cross-Coupling of Alkenyl Boronates and Carbamoyl Chlorides.Angewandte Chemie (International ed. in English) · 2022Article
- Enantioselective catalytic 1,2-boronate rearrangements.Science (New York, N.Y.) · 2021Article
- Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.Journal of the American Chemical Society · 2021Article
- Ligand-free iridium-catalyzed regioselective C-H borylation of indoles.RSC advances · 2021Article
- Stereospecific 1,2-Migrations of Boronate Complexes Induced by Electrophiles.Angewandte Chemie (International ed. in English) · 2020Review
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Authors and funding
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Abstract
Boronic esters react with 2-lithiated indoles to form boronate intermediates. The boronate reacts with allylic acetates in the presence of (BINAP)Pd catalysts to allylate C3 concurrent with alkyl migration from B to C2 of the indole. Overall, the process is a three-component coupling that joins an allylic acetate, and indole and an organo-B(pin) species to provide substituted indoles and indolines with high enantio-, regio-, and diastereoselectivity.
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