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Abstract
After optimization for retention of catalytic activity, 4-chlorobenzoic acid emerged as the optimal catalyst for the aliphatic ketone Claisen rearrangement. The optimal catalyst enables a one-pot, metal-free, catalytic protocol from allylic alcohols to γ,δ-unsaturated ketones. The optimized process tolerates a range of substrates, including substituents with acid-labile protecting groups. Reaction monitoring and DFT studies of the aliphatic ketone Claisen process agree that the ultimate rearrangement step typically has the highest activation barrier.
Original language | English |
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Article number | e202402371 |
Number of pages | 6 |
Journal | Chemistry - A European Journal |
Volume | 30 |
Issue number | 53 |
DOIs | |
Publication status | Published - 19 Sept 2024 |
MoE publication type | A1 Journal article-refereed |
Keywords
- Acid catalysis
- Claisen rearrangement
- Reaction optimization
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Dive into the research topics of 'Aliphatic Ketone Claisen Rearrangement: Troubleshooting the Transetherification Step by Identifying a Stable Acid Catalyst'. Together they form a unique fingerprint.Projects
- 1 Finished
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XAI-BAT-Aka: Materials Development for Flow Batteries with Help of Explainable AI
Laasonen, K. (Principal investigator), Farshadfar, K. (Project Member), Mahdian, A. (Project Member), Khakpour, R. (Project Member) & Mäkinen, M. (Project Member)
EU The Recovery and Resilience Facility (RRF)
01/01/2022 → 31/12/2024
Project: Academy of Finland: Other research funding