ArticleJournal of the American Chemical Society2020
The Transition Metal Catalyzed [π2s + π2s + σ2s + σ2s] Pericyclic Reaction: Woodward-Hoffmann Rules, Aromaticity, and Electron Flow.
Article in Journal of the American Chemical Society, 2020. 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.
- Enantioselective Michael Spirocyclization of Palladium Enolates.ACS catalysis · 2025Article
- Electron Dynamics in Alkane C-H Activation Mediated by Transition Metal Complexes.The journal of physical chemistry. A · 2024Article
- The application of aromaticity and antiaromaticity to reaction mechanisms.Fundamental research · 2023Review
- Origins of Enhanced Enantioselectivity in the Pd-Catalyzed Decarboxylative Allylic Alkylation ofCatalysts (Basel, Switzerland) · 2023Article
- Hafnium(IV) Chemistry with Imide-Dioxime and Catecholate-Oxime Ligands: Unique {HfInorganic chemistry · 2022Article
- Understanding chemistry: from "heuristic (soft) explanations and reasoning by analogy" to "quantum chemistry".Chemical science · 2022Review
- Electrophilic aromatic substitution reactions of compounds with Craig-Möbius aromaticity.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
- Ti-Catalyzed and -Mediated Oxidative Amination Reactions.Accounts of chemical research · 2021Article
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Authors and funding
3 authors.
Funding
Abstract
We have shown that the fundamental step responsible for enantioinduction in the inner-sphere asymmetric Tsuji allylic alkylation is C-C bond formation through a seven-membered pericyclic transition state. We employ an extensive series of quantum mechanics (QM) calculations to delineate how the electronic structure of the Pd-catalyzed C-C bond forming process controls the reaction. Phase inversion introduced by d orbitals renders the Pd-catalyzed [π2s + π2s + σ2s + σ2s] reaction symmetry-allowed in the ground state, proceeding through a transition state with Craig-Möbius-like σ-aromaticity. Lastly, we connect QM to fundamental valence bonding concepts by deriving an ab initio "arrow-pushing" mechanism that describes the flow of electron density through the reaction.
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