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银(I)作为一种广泛适用的均相催化剂,用于在水中将醛有氧氧化为羧酸——“银镜”:从化学计量到催化。

Silver(I) as a widely applicable, homogeneous catalyst for aerobic oxidation of aldehydes toward carboxylic acids in water-"silver mirror": From stoichiometric to catalytic.

作者信息

Liu Mingxin, Wang Haining, Zeng Huiying, Li Chao-Jun

机构信息

Department of Chemistry and FRQNT Centre in Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.

出版信息

Sci Adv. 2015 Mar 27;1(2):e1500020. doi: 10.1126/sciadv.1500020. eCollection 2015 Mar.

Abstract

The first example of a homogeneous silver(I)-catalyzed aerobic oxidation of aldehydes in water is reported. More than 50 examples of different aliphatic and aromatic aldehydes, including natural products, were tested, and all of them successfully underwent aerobic oxidation to give the corresponding carboxylic acids in extremely high yields. The reaction conditions are very mild and greener, requiring only a very low silver(I) catalyst loading, using atmospheric oxygen as the oxidant and water as the solvent, and allowing gram-scale oxidation with only 2 mg of our catalyst. Chromatography is completely unnecessary for purification in most cases.

摘要

报道了首例在水中均相银(I)催化的醛的有氧氧化反应。测试了50多个不同的脂肪族和芳香族醛的例子,包括天然产物,所有这些醛都成功地进行了有氧氧化,以极高的产率得到相应的羧酸。反应条件非常温和且更环保,仅需极低的银(I)催化剂负载量,使用大气中的氧气作为氧化剂,水作为溶剂,仅用2毫克我们的催化剂就能实现克级氧化。在大多数情况下,完全不需要色谱法进行纯化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/98e8/4643818/d161ddaa2356/1500020-F1.jpg

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