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以HO作为氢的替代物,铁催化α,β-不饱和酮的化学选择性转移氢化反应

Iron-Catalyzed Chemoselective Transfer Hydrogenation of α,β-Unsaturated Ketones Using HO as a Surrogate of Hydrogen.

作者信息

Manisha Manisha, Kumari Sangeeta, Sharma Deepak, Negi Lalit, Joshi Raj K

机构信息

Department of Chemistry, Malaviya National Institute of Technology Jaipur, JLN Marg, Jaipur 302017, Rajasthan, India.

出版信息

J Org Chem. 2024 Sep 6;89(17):11983-11993. doi: 10.1021/acs.joc.4c00601. Epub 2024 Aug 18.

Abstract

Sustainable and highly economical iron-catalyzed chemoselective reduction of C═C of α,β-unsaturated ketones has been established under mild reaction protocols. Water is used as a green and abundant surrogate of hydrogen and is scarcely used in organic synthetic transformations as a source of hydrogen. The developed protocol offers a broad spectrum for chemoselective transfer hydrogenation of α,β-unsaturated ketones. Moreover, the method was found to be highly effective for aryl and ferrocenyl α,β-unsaturated ketones consisting of one or two double bonds and with multiple functionalities. Moreover, the present method avoids prolonged reaction time, provides a wide range of substrates with excellent yield, and circumvents the tedious chromatographic workup.

摘要

在温和的反应条件下,已实现了可持续且经济高效的铁催化α,β-不饱和酮碳碳双键的化学选择性还原。水被用作绿色且丰富的氢替代物,在有机合成转化中很少作为氢源使用。所开发的方法为α,β-不饱和酮的化学选择性转移氢化提供了广泛的适用范围。此外,该方法被发现对含有一个或两个双键且具有多种官能团的芳基和二茂铁基α,β-不饱和酮非常有效。而且,本方法避免了反应时间过长的问题,能以优异的产率提供多种底物,并且避免了繁琐的柱色谱后处理。

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