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使用三氟甲磺酸铁(Fe(OTf)₃)和硼氢化钠(NaBH₄)进行铁催化、通用且操作简单的形式氢化反应。

Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4.

作者信息

MacNair Alistair J, Tran Ming-Ming, Nelson Jennifer E, Sloan G Usherwood, Ironmonger Alan, Thomas Stephen P

机构信息

School of Chemistry, University of Edinburgh, Joseph Black Building, West Mains Road, Edinburgh EH9 3JJ, UK.

出版信息

Org Biomol Chem. 2014 Jul 28;12(28):5082-8. doi: 10.1039/c4ob00945b.

DOI:10.1039/c4ob00945b
PMID:24914735
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4295815/
Abstract

An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.

摘要

已开发出一种操作简单且环境友好的形式氢化方案,该方案使用高丰度的铁(III)盐和一种廉价、在实验室条件下稳定的化学计量还原剂硼氢化钠(NaBH4),在乙醇中于环境条件下进行反应。该反应已应用于末端烯烃的还原(22个实例,产率高达95%)和硝基的还原(26个实例,产率高达95%)。氘标记研究表明,该反应通过离子机制而非自由基机制进行。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b063/4295815/2e6037cd263b/c4ob00945b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b063/4295815/7a94b4e9a732/c4ob00945b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b063/4295815/fda549b62bea/c4ob00945b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b063/4295815/2e6037cd263b/c4ob00945b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b063/4295815/7a94b4e9a732/c4ob00945b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b063/4295815/fda549b62bea/c4ob00945b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b063/4295815/2e6037cd263b/c4ob00945b-s3.jpg

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