ArticleNature chemistry2022
Catalytic remote hydrohalogenation of internal alkenes.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 52 citations in OpenAlex.
- Palladium-catalyzed enantioselective alkenylation of acyclic alkenols: Broad scope with alkenyl bromides.Science advances · 2026Article
- Contra-Thermodynamic Chain-Walking Isomerization: A Sustainable Tool for Selective Molecular Editing in Green Chemistry.ChemSusChem · 2026Article
- Dual engineering of thermodynamics and kinetics in covalent organic frameworks for separation.Nature communications · 2026Article
- Regiocontrolled hydrobromination of unactivated alkenes via direct and chain-walking pathways.Science advances · 2025Article
- Article
- Anti-Markovnikov hydro- and deuterochlorination of unsaturated hydrocarbons using iron photocatalysis.Nature synthesis · 2025Article
- Palladium-catalyzed remote internal C(spNature communications · 2024Article
- Controllable Multihalogenation of a Non-native Substrate by the SyrB2 Iron Halogenase.ACS catalysis · 2024Article
- Direct Construction of C-Alkyl Glycosides from Non-Activated Olefins via Nickel-Catalyzed C(spAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Tuning light-driven oxidation of styrene inside water-soluble nanocages.Nature communications · 2024Article
- Advancements in hydrochlorination of alkenes.Beilstein journal of organic chemistry · 2024Review
- Multi-site programmable functionalization of alkenes via controllable alkene isomerization.Nature chemistry · 2023Article
- Asymmetric intermolecular allylic C-H amination of alkenes with aliphatic amines.Science (New York, N.Y.) · 2022Article
- Palladium-catalysed efficient synthesis of primary alkyl halides from terminal and internal alkenes.National science review · 2022Article
- Photo-Induced Halogen-Atom Transfer: Generation of Halide Radicals for Selective Hydrohalogenation Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Primary alkyl halides have broad utility as fine chemicals in organic synthesis. The direct halogenation of alkenes is one of the most efficient approaches for the synthesis of these halides. Internal alkenes, in particular mixtures of isomers from refineries, constitute readily available and inexpensive feedstock and are the most attractive starting materials for this synthesis. However, the hydrohalogenation of alkenes generally affords branched alkyl halides; there are no catalytic methods to prepare linear alkyl halides directly from internal alkenes, let alone from a mixture of alkene isomers. Here we report the remote oxidative halogenation of alkenes under palladium catalysis via which both terminal and internal alkenes yield primary alkyl halides efficiently. Engineering pyridine-oxazoline ligands by introducing a hydroxyl group is essential for achieving excellent chemo- and regioselectivity. The catalytic system is also good for the mixture of alkene isomers generated from dehydrogenation of alkanes, providing a window to investigate the high-value utilization of inexpensive alkanes.
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