Abstract
Herein we report an intramolecular endo-selective Heck reaction of iodomethylsilyl ethers of phenols and alkenols. The reaction leads to the formation of seven- and eight-membered siloxycycles in excellent yields which could be further converted into the corresponding allylic alcohols upon oxidation. Thus, the method could be used for the selective (Z)-hydroxymethylation of o-hydroxystyrenes and alkenols. Rapid scan EPR experiments and DFT calculations suggests a concerted β-hydrogen elimination event to take place in the triplet state.
| Original language | English (US) |
|---|---|
| Journal | Chemical Communications |
| DOIs | |
| State | Published - Feb 24 2023 |
| Externally published | Yes |
Bibliographical note
KAUST Repository Item: Exported on 2023-03-01Acknowledgements: This work has been finically supported by Deutsche Forschungsgemeinschaft (DFG, grant number 456582392) and by Leibniz institute for catalysis e.V (LIKAT Rostock). E. J. E.-S acknowledges the Erasmus Munds program of EU (SusCat) for the master scholarship. H.T.D. thanks RoHan SDG Graduate School funded by the German Academic Exchange Service (DAAD, 57315854) for postdoctoral fellowship. L.M.A. is Ramón y Cajal fellow (ref. RYC2021-030994-I) and thanks MCIN/AEI and NextGenerationEU/PRTR for support and the KAUST Supercomputer Laboratory (KSL) for providing the computational resources (Shaheen II). O.E.-S. gratefully thanks Prof. Dr. Matthias Beller for his continued generous support.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.
ASJC Scopus subject areas
- Materials Chemistry
- Surfaces, Coatings and Films
- Metals and Alloys
- Ceramics and Composites
- General Chemistry
- Catalysis
- Electronic, Optical and Magnetic Materials