Efficient Catalyst-Free Henry Reaction between Nitroalkanes and Aldehydes or Trifluoromethyl Ketones Promoted by Tap Water
Efficient Catalyst-Free Henry Reaction between Nitroalkanes and Aldehydes or Trifluoromethyl Ketones Promoted by Tap Water
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DOI：
10.1055/a-1933-3709
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发表时间：
2022-09-28
影响因子：
2.6
通讯作者：
Da, Chao-Shan
中科院分区：
文献类型：
--
作者：
Du, Zhi-Hong;Yuan, Meng;Da, Chao-Shan
报道了硝基烷烃与醛或三氟甲基酮之间在无催化剂和无添加剂条件下、在可回收自来水介质中和在室温下进行的高效亨利反应的第一个例子。该工艺可耐受多种醛类和三氟甲基酮类，以极好的收率生产一系列β -硝基醇产品。这类产品广泛用于医药中间体和天然产物的合成。该方案可以成功地扩大到50毫摩尔的规模，而不会降低产量。中国不同地区自来水的pH值在7.5 ~ 8.1之间，但pH值的变化对产量没有影响，并成功地再现了这一过程。最后，即使反应基质不同，自来水也可以有效地回收再利用，而无需任何后处理。
The first examples of highly effective Henry reactions between nitroalkanes and aldehydes or trifluoromethyl ketones that proceed under catalyst-free and additive-free conditions, in a recyclable tap water medium, and at room temperature are reported. This process tolerates a broad range of aldehydes and trifluoromethyl ketones to give a series of beta-nitro alcohol products in excellent yields. Such products are widely used in the syntheses of pharmaceutical intermediates and natural products. This protocol can be successfully scaled up to a 50-mmol scale without a reduction in yield. Tap water from different locations in China exhibited pH values ranging from 7.5 to 8.1, but the varying pH had no effect on the yield and the processes were successfully reproduced. Finally, the tap water was effectively recovered and reused without any postprocessing, even when the reaction substrates were different.