ArticleNature communications2024
Amide C-N bonds activation by A new variant of bifunctional N-heterocyclic carbene.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Persistent Solid-State Bipyridine Atropisomerism in a Ferrocenyl-Functionalized Chiral BINOL Scaffold.Crystal growth & design · 2026Article
- Access to C─N and N─N Axially Chiral Pyridinones via NHC-Catalyzed Dynamic Kinetic Resolution of Rotationally Restricted Cyclic Imides.Angewandte Chemie (International ed. in English) · 2026Article
- Enantioselective synthesis of ring-constrained biaryls via a twist-expand-seal strategy.Nature communications · 2026Article
- Pd(II)-NHC (NHC = N-Heterocyclic Carbene)-Catalyzed Alkylation of Primary Amides by Site-Selective N─C(O) Activation.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Efficient Synthesis of Amides through Thioacids Reactions with In Situ Generated Formamidine.The Journal of organic chemistry · 2025Article
- Stereoselective diversification of α-amino acids enabled by N-heterocyclic carbene catalysis.Nature communications · 2025Article
- Organocatalyzed atroposelective dynamic kinetic resolutions via transient seven-membered cyclic hemiacetals.Science advances · 2025Article
- Bifunctional Catalysis of Aldol Reactions by Foldamer Dihydrazides: Assessment of Conformational Preorganization.Journal of the American Chemical Society · 2025Article
- Desymmetric esterification catalysed by bifunctional chiral N-heterocyclic carbenes provides access to inherently chiral calix[4]arenes.Nature communications · 2025Article
- Enantioselective synthesis of saddle-shaped eight-membered lactones with inherent chirality via organocatalytic high-order annulation.Nature communications · 2024Article
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Authors and funding
7 authors.
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Abstract
We report an organocatalyst that combines a triazolium N-heterocyclic carbene (NHC) with a squaramide as a hydrogen-bonding donor (HBD), which can effectively catalyze the atroposelective ring-opening of biaryl lactams via a unique amide C-N bond cleavage mode. The free carbene species attacks the amide carbonyl, forming an axially chiral acyl-azolium intermediate. Various axially chiral biaryl amines can be accessed by this methodology with up to 99% ee and 99% yield. By using mercaptan as a catalyst turnover agent, the resulting thioester synthon can be transformed into several interesting atropisomers. Both control experiments and theoretical calculations reveal the crucial role of the hybrid NHC-HBD skeleton, which activates the amide via H-bonding and brings it spatially close to the carbene centre. This discovery illustrates the potential of the NHC-HBD chimera and demonstrates a complementary strategy for amide bond activation and manipulation.
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