ArticleAngewandte Chemie (International ed. in English)2021
Activation of 2-Cyclohexenone by BF
Article in Angewandte Chemie (International ed. in English), 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.
- A radical-polar crossover approach to complex nitrogen heterocycles via the triplet state.Chem · 2026Article
- Enantioselective Photochemical Generation of a Short-Lived, Twisted Cycloheptenone Isomer: Catalytic Formation, Detection, and Consecutive Chemistry.Angewandte Chemie (International ed. in English) · 2025Article
- Catalytic Enantioselective 6π Photocyclization of Acrylanilides.Journal of the American Chemical Society · 2023Article
- Time-resolved X-ray and XUV based spectroscopic methods for nonadiabatic processes in photochemistry.Chemical communications (Cambridge, England) · 2022Review
- Visible Light-Mediated Dearomative Hydrogen Atom Abstraction/ Cyclization Cascade of Indoles.Angewandte Chemie (International ed. in English) · 2022Article
- Enantioselective crossed intramolecular [2+2] photocycloaddition reactions mediated by a chiral chelating Lewis acid.Chemical science · 2022Article
- Fluorescence-Detected Pump-Probe Spectroscopy.Angewandte Chemie (International ed. in English) · 2021Article
- Activation of 2-Cyclohexenone by BFAngewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Lewis acids have recently been recognized as catalysts enabling enantioselective photochemical transformations. Mechanistic studies on these systems are however rare, either due to their absorption at wavelengths shorter than 260 nm, or due to the limitations of theoretical dynamic studies for larger complexes. In this work, we overcome these challenges and employ sub-30-fs transient absorption in the UV, in combination with a highly accurate theoretical treatment on the XMS-CASPT2 level. We investigate 2-cyclohexenone and its complex to boron trifluoride and analyze the observed dynamics based on trajectory calculations including non-adiabatic coupling and intersystem crossing. This approach explains all ultrafast decay pathways observed in the complex. We show that the Lewis acid remains attached to the substrate in the triplet state, which in turn explains why chiral boron-based Lewis acids induce a high enantioselectivity in photocycloaddition reactions.
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Registered trials
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