ArticleJournal of the American Chemical Society2022
Copper-Catalyzed Coupling of Alkyl Vicinal Bis(boronic Esters) to an Array of Electrophiles.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Selective Copper-Catalyzed Cross-Coupling of Cyclopropyl and Cyclobutyl 1,2-Bis(boronates).Organic letters · 2026Article
- Converting 1,1-Bisborylalkanes into 1,2-Bisborylalkanes Enabled by Iron Ligand-to-Metal Charge Transfer (LMCT) Photocatalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Asymmetric Synthesis of Propargylic and Allenic Silanes, Germanes, and Stannanes.Chemistry, an Asian journal · 2025Review
- Radical Strategy to the Boron-to-Copper Transmetalation Problem:Journal of the American Chemical Society · 2025Article
- Interlocking Pseudorotaxanes through Borane- and Boronic Ester-Mediated Carbon-Carbon Bond Formation.Organic letters · 2025Article
- Tandem Diboration-Protoboration of Terminal Alkynes: A Practical Route to α-Substituted Alkenyl Boronates.Synlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Iridium-Catalyzed Stereocontrolled C(spJournal of the American Chemical Society · 2025Article
- Iterative Catalyst-Controlled Diastereoselective Matteson Homologations Enable the Selective Synthesis of Benzestrol Isomers.Journal of the American Chemical Society · 2024Article
- Site-Selective Activation and Stereospecific Functionalization of Bis(boronic Esters) Derived from 2-Alkenes: Construction of Propionates and Other 1,2-Difunctional Motifs.Angewandte Chemie (International ed. in English) · 2024Article
- Chemoselective Cu-Catalyzed Cross-Nucleophile Alkylarylation of Alkenes.ACS catalysis · 2024Article
- Article
- Stereospecific Phosphination and Thioetherification of Organoboronic Esters.Journal of the American Chemical Society · 2024Article
- Platinum-Catalyzed Enantioselective Diboration of Monosubstituted Alkenes.Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2024Article
- Catalytic stereodivergent allylic alkylation of 2-acylimidazoles for natural product synthesis.Nature communications · 2023Article
- Base-mediated C-B bond activation of benzylic boronate for the rapid construction of β-silyl/boryl functionalized 1,1-diarylalkanes from aromatic alkenes.Chemical science · 2023Article
- 1,2-Diborylsilanes: Catalytic Enantioselective Synthesis and Site-Selective Cross-Coupling.ACS catalysis · 2023Article
- Stereospecific Transformations of Alkylboronic Esters Enabled by Direct Boron-to-Zinc Transmetalation.Journal of the American Chemical Society · 2023Article
- Desymmetrization of Vicinal Bis(boronic) Esters by Enantioselective Suzuki-Miyaura Cross-Coupling Reaction.Journal of the American Chemical Society · 2023Article
- Updated Progress of the Copper-Catalyzed Borylative Functionalization of Unsaturated Molecules.Molecules (Basel, Switzerland) · 2023Review
- Enantioselective Suzuki cross-coupling of 1,2-diboryl cyclopropanes.Chemical science · 2023Article
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Authors and funding
5 authors.
Funding
Abstract
A neighboring boronate group in the substrate provides a dramatic rate acceleration in transmetalation to copper and thereby enables organoboronic esters to participate in unprecedented site-selective cross-couplings. This cross-coupling operates under practical experimental conditions and allows for coupling between vicinal bis(boronic esters) and allyl, alkynyl, and propargyl electrophiles as well as a simple proton. Because the reactive substrates are vicinal bis(boronic esters), the cross-coupling described herein provides an expedient new method for the construction of boron-containing reaction products from alkenes. Mechanistic experiments suggest that chelated cyclic ate complexes may play a role in the transmetalation.
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