一种新型钯基催化体系,用于一锅选择性还原硝基苯羰基化形成 N-(4-羟基苯基)乙酰胺

Reactions Pub Date : 2023-11-17 DOI:10.3390/reactions4040042
A. Vavasori, Marco Capponi, L. Ronchin
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引用次数: 0

摘要

N-(4-羟基苯基)乙酰胺(俗称扑热息痛或对乙酰氨基酚)是许多生产医药用化学品的行业的目标分子。然而,工业生产过程采用多步骤工艺,总体收率低,而且/或者在可持续性方面存在严重缺陷和问题。本文提出了一种基于钯(II)络合物催化的硝基苯还原羰基化的单锅合成方法。通常,这种反应会产生不同产物的混合物,包括苯胺、4-氨基苯酚和 1,3-二苯基脲。然而,对可能产物的选择性在很大程度上取决于钯(II)催化剂上的配体,也取决于溶剂的性质。据此,我们发现当反应在稀醋酸溶剂中进行时,[PdCl2(dppb)] 催化剂前驱体在一锅中就能生成 N-(4-羟基苯基)乙酰胺。在优化的反应条件下,大约 5 小时就可以生产出选择性为 85 摩尔%的 N-(4-羟基苯基)乙酰胺。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
A New Pd-Based Catalytic System for the Reductive Carbonylation of Nitrobenzene to Form N-(4-hydroxyphenyl)acetamide Selectively in One Pot
N-(4-hydroxyphenyl)acetamide (commonly named paracetamol or acetaminophen) is a target molecules for many industries that produce chemicals for pharmaceutical applications. The industrial processes, however, use multistep procedures with low overall yield and/or severe drawbacks and problems in terms of sustainability. In the present paper, a one-pot synthesis is proposed based on the reductive carbonylation of nitrobenzene catalyzed by Pd(II)-complexes. Usually, such a reaction leads to a mixture of different products, including aniline, 4-aminophenol and 1,3-diphenylurea. However, the selectivity towards the possible products strongly depends by the ligands on the Pd(II)-catalyst, but also by the nature of the solvent. According to this, we have found that when the reaction was carried out in dilute acetic acid as a solvent, the [PdCl2(dppb)] catalyst precursor leads in one pot to N-(4-hydroxyphenyl)acetamide. Under optimized reaction conditions, it was possible to produce N-(4-hydroxyphenyl)acetamide with a 85 mol % of selectivity in ca. 5 h.
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CiteScore
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