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钪催化下以硅烷为还原剂实现醇的高选择性脱氧反应

Scandium-Catalyzed Highly Selective Deoxygenation of Alcohols by Using Hydrosilanes as Reductants.

作者信息

Buhaibeh Ruqaya, Thyagarajan Neethu, Bousrez Guillaume, Monsigny Louis, Cantat Thibault, Nicolas Emmanuel

机构信息

Université Paris-Saclay, CEA, CNRS, NIMBE, Gif-sur-Yvette, 91191, France.

出版信息

Chemistry. 2025 Jul 17;31(40):e202501596. doi: 10.1002/chem.202501596. Epub 2025 Jun 30.

DOI:10.1002/chem.202501596
PMID:40537408
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12272014/
Abstract

Herein, we present a straightforward and efficient scandium-based catalytic system that enables highly selective reduction of σ bonds (C─O) in the presence of more reactive π (C═O) or O─H bonds. Employing 5 mol% of Sc(OTf) as the catalyst, a diverse range of aryl and alkyl hydrosilanes proved to be highly effective in reducing secondary and tertiary alcohols to the corresponding alkanes. Furthermore, this protocol was extended to the deoxygenation of ketones and the hydrodehalogenation of alkyl halides.

摘要

在此，我们展示了一种简单高效的钪基催化体系，该体系能够在更具反应性的π键（C═O）或O─H键存在的情况下，实现对σ键（C─O）的高选择性还原。以5摩尔%的Sc(OTf)作为催化剂，多种芳基和烷基硅烷在将仲醇和叔醇还原为相应烷烃方面表现出高效性。此外，该方法还扩展到了酮的脱氧反应以及卤代烃的加氢脱卤反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/54ae569cc553/CHEM-31-e202501596-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/2d36f1ada429/CHEM-31-e202501596-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/25822a433848/CHEM-31-e202501596-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/5014df9f7e78/CHEM-31-e202501596-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/38f529d9032f/CHEM-31-e202501596-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/79f82c71c67d/CHEM-31-e202501596-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/0ed54abaa75d/CHEM-31-e202501596-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/e5f9d6b99d2a/CHEM-31-e202501596-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/54ae569cc553/CHEM-31-e202501596-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/2d36f1ada429/CHEM-31-e202501596-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/25822a433848/CHEM-31-e202501596-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/5014df9f7e78/CHEM-31-e202501596-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/38f529d9032f/CHEM-31-e202501596-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/79f82c71c67d/CHEM-31-e202501596-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/0ed54abaa75d/CHEM-31-e202501596-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/e5f9d6b99d2a/CHEM-31-e202501596-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c93e/12272014/54ae569cc553/CHEM-31-e202501596-g008.jpg

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本文引用的文献

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Arenium-ion-catalysed halodealkylation of fully alkylated silanes.芳鎓离子催化的全烷基化硅烷的卤代烷基化反应。
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