ArticleNature communications2021
Divergent rhodium-catalyzed electrochemical vinylic C-H annulation of acrylamides with alkynes.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Electrooxidative Divergent Halocyclizations of Ambident Amides.Angewandte Chemie (International ed. in English) · 2026Article
- Cathodic oxygen reduction-enabled rhodium-catalyzed (5 + 1) C-H/O-H annulation inspired by fuel cells.Nature communications · 2025Article
- Electrochemical cyclization of alkynes to construct five-membered nitrogen-heterocyclic rings.Beilstein journal of organic chemistry · 2025Review
- Synthesis of 1-Azatriene Complexes of Tungsten: Metal-Promoted Ring-Opening of Dihydropyridine.Organometallics · 2024Article
- Bifurcated Rhodaelectro-catalyzed C-H Activation for the Synthesis of Pyrroles and Lactones.Precision chemistry · 2023Article
- Silver-Free C-H Activation: Strategic Approaches towards Realizing the Full Potential of C-H Activation in Sustainable Organic Synthesis.Angewandte Chemie (International ed. in English) · 2022Review
- A Strategy for Site- and Chemoselective C-H Alkenylation through Osmaelectrooxidative Catalysis.Angewandte Chemie (International ed. in English) · 2021Article
- On the application of 3d metals for C-H activation toward bioactive compounds: The key step for the synthesis of silver bullets.Beilstein journal of organic chemistry · 2021Review
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7 authors.
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Abstract
α-Pyridones and α-pyrones are ubiquitous structural motifs found in natural products and biologically active small molecules. Here, we report an Rh-catalyzed electrochemical vinylic C-H annulation of acrylamides with alkynes, affording cyclic products in good to excellent yield. Divergent syntheses of α-pyridones and cyclic imidates are accomplished by employing N-phenyl acrylamides and N-tosyl acrylamides as substrates, respectively. Additionally, excellent regioselectivities are achieved when using unsymmetrical alkynes. This electrochemical process is environmentally benign compared to traditional transition metal-catalyzed C-H annulations because it avoids the use of stoichiometric metal oxidants. DFT calculations elucidated the reaction mechanism and origins of substituent-controlled chemoselectivity. The sequential C-H activation and alkyne insertion under rhodium catalysis leads to the seven-membered ring vinyl-rhodium intermediate. This intermediate undergoes either the classic neutral concerted reductive elimination to produce α-pyridones, or the ionic stepwise pathway to produce cyclic imidates.
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