ArticleScience (New York, N.Y.)2023
Rhodium catalyzed tunable amide homologation through a hook-and-slide strategy.
Article in Science (New York, N.Y.), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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The trial behind it
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Who cites it
16 citing papers in PubMed.
- Article
- Article
- Dynamic Imine-Linked NIPU with Shape Memory, Self-Healing, and Prospects for Recyclability.Polymers · 2026Article
- Amide synthesis via molecular shuffling of carboxylic acids.Nature communications · 2026Article
- Oxidative Arene Ring-Opening of Benzylic Alcohols.JACS Au · 2026Article
- A unified strategy for remote C-H fluorination of phenylacetic acids and their homologues at theChemical science · 2026Article
- Precise borylation of targeted methyl group via an orderly chain-walking strategy.Science advances · 2026Article
- Homologative alkene difunctionalization.Nature chemistry · 2026Article
- Modular esterification of unstrained carbonyls through palladium-catalyzed alkyne bridging C-C bond activation.Nature communications · 2025Article
- "Cut-and-Sew" Reactions of β-Lactams via C-C Bond Activation.Journal of the American Chemical Society · 2025Article
- Article
- One-carbon homologation of alkenes.Nature · 2025Article
- Insertion of anthranilyl unit into inert amides: A facile route to oligoamides and cyclic peptides.Science advances · 2025Article
- Skeletal Rearrangements of Amides via Breaking Inert Bonds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Skeletal Modification via Activation of Relatively Unstrained C-C Bonds.Accounts of chemical research · 2025Article
- Iterative One-Carbon Homologation of Unmodified Carboxylic Acids.Journal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Preparation of diverse homologs from lead compounds has been a common and important practice in medicinal chemistry. However, homologation of carboxylic acid derivatives, particularly amides, remains challenging. Here we report a hook-and-slide strategy for homologation of tertiary amides with tunable lengths of the inserted carbon chain. Alkylation at the α-position of the amide (hook) is followed by highly selective branched-to-linear isomerization (slide) to effect amide migration to the end of the newly introduced alkyl chain; thus, the choice of alkylation reagent sets the homologation length. The key step involves a carbon-carbon bond activation process by a carbene-coordinated rhodium complex with assistance from a removable directing group. The approach is demonstrated for introduction of chains as long as 16 carbons and is applicable to derivatized carboxylic acids in complex bioactive molecules.
Identifiers
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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.