ArticleJournal of the American Chemical Society2017
Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles.
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 18 papers.
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The trial behind it
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Who cites it
18 citing papers in PubMed.
- Control of axial stereochemistry for the enantioselective construction of a QUINAP library.Chemical science · 2026Article
- Eschenmoser's salts: from design to applications in organic synthesis.Organic chemistry frontiers : an international journal of organic chemistry · 2026Review
- Regioselective Electrochemical Borylation of Oxygenated Allylic Electrophiles: Method Development and Synthetic Applications.ACS central science · 2025Article
- Iridium-Catalyzed Stereocontrolled C(spJournal of the American Chemical Society · 2025Article
- Merging Organocatalysis with 1,2-Boronate Rearrangement: A Lewis Base-Catalyzed Asymmetric Multicomponent Reaction.Journal of the American Chemical Society · 2024Article
- Simultaneous Stereoinvertive and Stereoselective C(spJournal of the American Chemical Society · 2024Article
- 1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols.The Journal of organic chemistry · 2023Article
- Reactions of Benzylboronate Nucleophiles.Synthesis · 2023Article
- Synthesis of Quaternary and Tertiary Carbon-Substituted Arenes by Lewis Base Promoted Site-Selective Coupling with Allylic Nucleophiles.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
- Sparteine-Free, Highly Stereoselective Construction of Complex Allylic Alcohols Using 1,2-Metallate Rearrangements.JACS Au · 2023Article
- A General Strategy for the Asymmetric Preparation of α-Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride- and Palladium-Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Sulfenofunctionalization of Chiral α-Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCFAngewandte Chemie (International ed. in English) · 2022Article
- Mechanistic Basis for the Iridium-Catalyzed Enantioselective Allylation of Alkenyl Boronates.Journal of the American Chemical Society · 2022Article
- Photo-induced trifunctionalization of bromostyrenes via remote radical migration reactions of tetracoordinate boron species.Nature communications · 2022Article
- Electrophilic Fluorination of Alkenes via Bora-Wagner-Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates.Angewandte Chemie (International ed. in English) · 2021Article
- Benzylation of Imines with Activated Boronate Nucleophiles.European journal of organic chemistry · 2019Article
- Radical-Polar Crossover Reactions of Dienylboronate Complexes: Synthesis of Functionalized Allylboronic Esters.Organic letters · 2018Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Allylboronic esters react readily with carbonyls and imines (π-electrophiles), but are unreactive toward a range of other electrophiles. By addition of an aryllithium, the corresponding allylboronate complexes display enhanced nucleophilicity, enabling addition to a range of electrophiles (tropylium, benzodithiolylium, activated pyridines, Eschenmoser's salt, Togni's reagent, Selectfluor, diisopropyl azodicarboxylate (DIAD), MeSX) in high regio- and stereocontrol. This protocol provides access to key new functionalities, including quaternary stereogenic centers bearing moieties such as fluorine and the trifluoromethyl group. The allylboronate complexes were determined to be 7 to 10 orders of magnitude more reactive than the parent boronic ester.
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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.