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钛介导的羧酸酰胺还原为伯胺与硼烷-氨。

Titanium-Mediated Reduction of Carboxamides to Amines with Borane-Ammonia.

机构信息

Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA.

出版信息

Molecules. 2023 Jun 6;28(12):4575. doi: 10.3390/molecules28124575.

Abstract

In this study, the successful titanium tetrachloride-catalyzed reduction of aldehydes, ketones, carboxylic acids, and nitriles with borane-ammonia was extended to the reduction (deoxygenation) of a variety of aromatic and aliphatic pri-, sec- and tert-carboxamides, by changing the stoichiometry of the catalyst and reductant. The corresponding amines were isolated in good to excellent yields, following a simple acid-base workup.

摘要

在这项研究中,成功地将四氯化钛催化的醛、酮、羧酸和腈与氨硼烷的还原反应扩展到了各种芳香族和脂肪族伯、仲和叔羧酸酰胺的还原(脱氧)反应,通过改变催化剂和还原剂的化学计量比。相应的胺在简单的酸碱处理后以良好到优异的收率分离出来。

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本文引用的文献

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A Safer Reduction of Carboxylic Acids with Titanium Catalysis.钛催化羧酸的更安全还原。
Org Lett. 2022 Nov 25;24(46):8481-8486. doi: 10.1021/acs.orglett.2c03326. Epub 2022 Nov 15.
3
TiCl-Catalyzed Hydroboration of Ketones with Ammonia Borane.TiCl催化的酮与氨硼烷的硼氢化反应。
J Org Chem. 2022 Oct 7;87(19):13259-13269. doi: 10.1021/acs.joc.2c01744. Epub 2022 Sep 12.
4
Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation.通过串联碘化/脱碘化反应一锅法硼化制备氨基硼烷
ACS Omega. 2022 Apr 14;7(16):14377-14389. doi: 10.1021/acsomega.2c01461. eCollection 2022 Apr 26.
6
Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids.氨硼烷作为羧酸直接酰胺化反应的催化剂。
Org Lett. 2021 Apr 16;23(8):2938-2942. doi: 10.1021/acs.orglett.1c00591. Epub 2021 Apr 7.

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