ArticleNature communications2020
Ru(II)Porphyrinate-based molecular nanoreactor for carbene insertion reactions and quantitative formation of rotaxanes by active-metal-template syntheses.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 16 citations in OpenAlex.
- Inverted metal-free active template synthesis of rotaxanes via axle‑mediated macrocyclization.Nature chemistry · 2026Article
- Design Rules for Sb and Bi Porphyrin Capsules: Para-Substitution Effects and Pnictogen Bond Conformational Control.Inorganic chemistry · 2026Article
- Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations.Angewandte Chemie (International ed. in English) · 2025Article
- Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins.Molecules (Basel, Switzerland) · 2023Review
- Functional group introduction and aromatic unit variation in a set of π-conjugated macrocycles: revealing the central role of local and global aromaticity.Organic chemistry frontiers : an international journal of organic chemistry · 2021Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Selectivity in N-H and S-H carbene insertion reactions promoted by Ru(II)porphyrinates currently requires slow addition of the diazo precursor and large excess of the primary amine and thiol substrates in the reaction medium. Such conditions are necessary to avoid the undesirable carbene coupling and/or multiple carbene insertions. Here, the authors demonstrate that the synergy between the steric shielding provided by a Ru(II)porphyrinate-based macrocycle with a relatively small central cavity and the kinetic stabilization of otherwise labile coordinative bonds, warranted by formation of the mechanical bond, enables single carbene insertions to occur with quantitative efficiency and perfect selectivity even in the presence of a large excess of the diazo precursor and stoichiometric amounts of the primary amine and thiol substrates. As the Ru(II)porphyrinate-based macrocycle bears a confining nanospace and alters the product distribution of the carbene insertion reactions when compared to that of its acyclic version, the former therefore functions as a nanoreactor.
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Registered trials
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