Aliphatic Ketone Claisen Rearrangement : Troubleshooting the Transetherification Step by Identifying a Stable Acid Catalyst
| dc.contributor.author | Pihko, Petri M. | |
| dc.contributor.author | Laasonen, Kari | |
| dc.contributor.author | Bruce, Veera Karoliina | |
| dc.contributor.author | Rolig, Aino | |
| dc.contributor.author | Farshadfar, Kaveh | |
| dc.date.accessioned | 2024-10-21T10:43:04Z | |
| dc.date.available | 2024-10-21T10:43:04Z | |
| dc.date.issued | 2024 | |
| dc.identifier.citation | Pihko, P. M., Laasonen, K., Bruce, V. K., Rolig, A., & Farshadfar, K. (2024). Aliphatic Ketone Claisen Rearrangement : Troubleshooting the Transetherification Step by Identifying a Stable Acid Catalyst. <i>Chemistry : A European Journal</i>, <i>30</i>(53), Article e202402371. <a href="https://doi.org/10.1002/chem.202402371" target="_blank">https://doi.org/10.1002/chem.202402371</a> | |
| dc.identifier.other | CONVID_233266963 | |
| dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/97564 | |
| dc.description.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. | en |
| dc.format.mimetype | application/pdf | |
| dc.language.iso | eng | |
| dc.publisher | Wiley-VCH Verlag | |
| dc.relation.ispartofseries | Chemistry : A European Journal | |
| dc.rights | CC BY 4.0 | |
| dc.subject.other | Claisen rearrangement | |
| dc.subject.other | acid catalysis | |
| dc.subject.other | reaction optimization | |
| dc.title | Aliphatic Ketone Claisen Rearrangement : Troubleshooting the Transetherification Step by Identifying a Stable Acid Catalyst | |
| dc.type | research article | |
| dc.identifier.urn | URN:NBN:fi:jyu-202410216426 | |
| dc.contributor.laitos | Kemian laitos | fi |
| dc.contributor.laitos | Department of Chemistry | en |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
| dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
| dc.description.reviewstatus | peerReviewed | |
| dc.relation.issn | 0947-6539 | |
| dc.relation.numberinseries | 53 | |
| dc.relation.volume | 30 | |
| dc.type.version | publishedVersion | |
| dc.rights.copyright | © 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH | |
| dc.rights.accesslevel | openAccess | fi |
| dc.type.publication | article | |
| dc.relation.grantnumber | 348328 | |
| dc.relation.grantnumber | 339892 | |
| dc.subject.yso | kemialliset reaktiot | |
| dc.subject.yso | katalyysi | |
| dc.subject.yso | katalyytit | |
| dc.subject.yso | ketonit | |
| dc.format.content | fulltext | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p3658 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p8704 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p15480 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p18652 | |
| dc.rights.url | https://creativecommons.org/licenses/by/4.0/ | |
| dc.relation.doi | 10.1002/chem.202402371 | |
| dc.relation.funder | Research Council of Finland | en |
| dc.relation.funder | Research Council of Finland | en |
| dc.relation.funder | Suomen Akatemia | fi |
| dc.relation.funder | Suomen Akatemia | fi |
| jyx.fundingprogram | Others, AoF | en |
| jyx.fundingprogram | Academy Project, AoF | en |
| jyx.fundingprogram | Muut, SA | fi |
| jyx.fundingprogram | Akatemiahanke, SA | fi |
| jyx.fundinginformation | This project has received funding from the European Union –Next Generation EU instrument via Research Council of Finland under grant numbers 348328 (to P.M.P.) and 348327 (K.L.), and funding from Research Council of Finland (grant and 339892 to P.M.P.) We also thank Dr. Leena Otsomaa and Dr. Mikko Passiniemi (Orion Oyj, Espoo, Finland) for additional laboratory resources and funding via the Orion iPhD program. | |
| dc.type.okm | A1 |
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