ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2024
Ligand Relay for Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Chlorides.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 24 citations in OpenAlex.
- Ligand relay catalysis enables asymmetric migratory dearomative annulation of N-heteroarenes.Nature communications · 2026Article
- Nickel-catalyzed hydroxymethylation with α-siliconChemical science · 2026Article
- Vanadium-Mediated Carbon Isotope Exchange of Terminal Alkenes.Journal of the American Chemical Society · 2025Article
- Cross-Electrophile Coupling to Form Sterically Hindered C(spJournal of the American Chemical Society · 2025Article
- Nickel-Catalyzed Reductive Cyanation of Aryl Halides and Epoxides with Cyanogen Bromide.Molecules (Basel, Switzerland) · 2024Article
- Ligand Relay for Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Chlorides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Transition metal-catalyzed direct decarboxylative transformations of aromatic carboxylic acids usually require high temperatures, which limit the substrate's scope, especially for late-stage applications. The development of the selective decarbonylative of carboxylic acid derivatives, especially the most fundamental aroyl chlorides, with stable and cheap electrophiles under mild conditions is highly desirable and meaningful, but remains challenging. Herein, a strategy of nickel-catalyzed decarbonylative alkylation of aroyl chlorides via phosphine/nitrogen ligand relay is reported. The simple phosphine ligand is found essential for the decarbonylation step, while the nitrogen ligand promotes the cross-electrophile coupling. Such a ligand relay system can effectively and orderly carry out the catalytic process at room temperature, utilizing easily available aroyl chlorides as an aryl electrophile for reductive alkylation. This discovery provides a new strategy for direct decarbonylative coupling, features operationally simple, mild conditions, and excellent functional group tolerance. The mild approach is applied to the late-stage methylation of various pharmaceuticals. Extensive experiments are carried out to provide insights into the reaction pathway and support the ligand relay process.
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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.