ArticleNature chemistry2019
Enantioselective construction of remote tertiary carbon-fluorine bonds.
Article in Nature chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
What it found
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Who cites it
21 citing papers in PubMed.
- Palladium-catalyzed asymmetric carbofluorination ofChemical communications (Cambridge, England) · 2026Article
- Alkyne migratory functionalization via C(spNature communications · 2026Article
- Ligand-controlled divergent enantioselective hydroarylation of cyclobutenes.Chemical science · 2025Article
- Enantioselective Construction of Fluorinated Tertiary Stereocenters by Rh-Catalyzed [2 + 2 + 2] Cycloaddition of 1,6-Enynes with α-Fluoroacrylamides.Organic letters · 2025Article
- Facile construction of distal and diversified tertiary and quaternary stereocenters.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Silver-Catalyzed (Journal of the American Chemical Society · 2024Article
- Organocatalytic Asymmetric Conjugate Addition of Fluorooxindoles to Quinone Methides.The Journal of organic chemistry · 2024Article
- Multi-site programmable functionalization of alkenes via controllable alkene isomerization.Nature chemistry · 2023Article
- Homologation of aryl ketones to long-chain ketones and aldehydes via C-C bond cleavage.iScience · 2022Article
- Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters.Chemical science · 2022Article
- Stereodefined alkenes with a fluoro-chloro terminus as a uniquely enabling compound class.Nature chemistry · 2022Article
- Palladium-catalyzed regio- and enantioselective migratory allylic C(spNature communications · 2021Article
- A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis.Journal of the American Chemical Society · 2021Article
- Stereoselective Remote Functionalization via Palladium-Catalyzed Redox-Relay Heck Methodologies.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization.Journal of the American Chemical Society · 2020Article
- Migratory functionalization of unactivated alkyl bromides for construction of all-carbon quaternary centers via transposed tert-C-radicals.Nature communications · 2020Article
- Copper-Catalyzed Defluorinative Borylation and Silylation ofOrganic letters · 2020Article
- Asymmetric synthesis of γ-chiral borylalkanesChemical science · 2020Article
- Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction.Journal of the American Chemical Society · 2020Article
- Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequentChemical science · 2020Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
The carbon-fluorine bond engenders distinctive physicochemical properties and significant changes to general reactivity. The development of catalytic, enantioselective methods to set stereocentres that contain a benzylic C-F bond is a rapidly evolving goal in synthetic chemistry. Although there have been notable advances that enable the construction of secondary stereocentres that contain both a C-F and a C-H bond on the same carbon, significantly fewer strategies are defined to access stereocentres that incorporate a tertiary C-F bond, especially those remote from pre-existing activating groups. Here we report a general method that establishes C-F tertiary benzylic stereocentres by forging a C-C bond via a Pd-catalysed enantioselective Heck reaction of acyclic alkenyl fluorides with arylboronic acids. This method provides a platform to rapidly incorporate significant functionality about the benzylic tertiary fluoride by virtue of the diversity of both reaction partners, as well as the ability to install the stereocentres remotely from pre-existing functional groups.
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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.