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芳香族和杂芳香族醛酮的无金属三氟甲基化反应。

Metal-free trifluoromethylation of aromatic and heteroaromatic aldehydes and ketones.

作者信息

Qiao Yupu, Si Tuda, Yang Ming-Hsiu, Altman Ryan A

机构信息

Department of Medicinal Chemistry, The University of Kansas , Lawrence, Kansas 66045, United States.

出版信息

J Org Chem. 2014 Aug 1;79(15):7122-31. doi: 10.1021/jo501289v. Epub 2014 Jul 15.

Abstract

The ability to convert simple and common substrates into fluoroalkyl derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic ketones and aldehydes into aryl and heteroaryl β,β,β-trifluoroethylarenes and -heteroarenes. The traditional approach for this net transformation involves stoichiometric metals and/or multistep reaction sequences that consume excessive time, material, and labor resources while providing low yields of products. To complement these traditional strategies, we report a one-pot metal-free decarboxylative procedure for accessing β,β,β-trifluoroethylarenes and -heteroarenes from readily available ketones and aldehydes. This method features several benefits, including ease of operation, readily available reagents, mild reaction conditions, high functional-group compatibility, and scalability.

摘要

在温和条件下将简单常见的底物转化为氟烷基衍生物的能力,仍然是药物化学家和农业化学家的一个重要目标。一个理想转化的代表性例子是将芳香族和杂芳香族酮及醛转化为芳基和杂芳基β,β,β-三氟乙基芳烃及杂芳烃。这种净转化的传统方法涉及化学计量的金属和/或多步反应序列,这会消耗过多的时间、材料和劳动力资源,同时产品收率较低。为了补充这些传统策略,我们报道了一种无金属的一锅法脱羧程序,可从易得的酮和醛制备β,β,β-三氟乙基芳烃及杂芳烃。该方法具有多个优点,包括操作简便、试剂易得、反应条件温和、官能团兼容性高以及可扩展性强。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3f96/4120972/d5955e985e57/jo-2014-01289v_0002.jpg

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