ArticleNature chemistry2021
Organocatalyst-controlled site-selective arene C-H functionalization.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Computational Thermodynamic and Kinetic Analysis of Meisenheimer Intermediate Formation in Aromatic Nucleophilic Addition.Molecules (Basel, Switzerland) · 2026Article
- Catalytic asymmetric formal nucleophilic C2-substitution of indoles via C2-umpolung toward 2,3'-bisindole atropisomers.Nature communications · 2026Article
- Pd-catalyzed sequential distal C-H alkenylation and π-allylic amination of arylacetic acids using MBH acetates: access to macrocyclic lactams.Chemical science · 2026Article
- Rh(II)-Catalyzed Selective C(spOrganic letters · 2024Article
- Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality.Precision chemistry · 2024Article
- Stereoselective synthesis of C3-tetrasubstituted oxindolesRSC advances · 2022Article
- Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls.Nature communications · 2022Article
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Authors and funding
10 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Over the past three decades, organocatalysis has emerged as a powerful catalysis platform and has gradually been incorporated into the routine synthetic toolbox to obtain chiral molecules. However, its application in the site- and enantioselective functionalization of inactive aryl C-H bonds remains in its infancy. Here, we present an organocatalyst-controlled para-selective arene C-H functionalization strategy that addresses this issue, which remains an enduring challenge in arene functionalization chemistry. By emulating enzyme catalysis, the chiral phosphoric acid catalyst offers an ideal chiral environment for stereoinduction, and the projecting substituents give control of chemo- and site-selectivity. Various types of nucleophile are compatible with this method, affording more than 100 para-selective adducts with stereodefined carbon centres or axes in viable molecular contexts. This protocol is expected to provide a general strategy for para-selective functionalization of arene C-H bonds in a controlled manner.
Identifiers
34373595What OpenQuestion holds
Registered trials
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