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1,3-二溴-5,5-二甲基乙内酰脲(DBH)介导的在水中由烯烃一锅法合成α-溴代/氨基酮。

1,3-Dibromo-5,5-dimethylhydantoin (DBH) mediated one-pot syntheses of α-bromo/amino ketones from alkenes in water.

作者信息

Xu Senhan, Wu Ping, Zhang Wei

机构信息

School of Pharmacy, Fudan University, Shanghai, China.

出版信息

Org Biomol Chem. 2016 Dec 28;14(48):11389-11395. doi: 10.1039/c6ob02200f. Epub 2016 Nov 18.

Abstract

α-Bromo ketones are versatile intermediates of high practical utility. Traditional approaches to these compounds are restricted to a relatively hazardous/complex reagent combination, a long reaction time, the use of non-environmentally friendly solvents, or a limited substrate scope. Herein, we describe the development of a new methodology for the preparation of α-bromo ketones from alkenes using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a bromine source and an oxidant simultaneously. This easy to carry out two-step one-pot protocol proceeds in water and provides high yield of a great variety of α-bromo ketones. Addition of an amine to the intermediate α-bromo ketone further enables the preparation of α-amino ketones in a one-pot sequence.

摘要

α-溴代酮是具有高度实用价值的多功能中间体。传统合成这些化合物的方法局限于相对危险/复杂的试剂组合、较长的反应时间、使用不环保的溶剂或底物范围有限。在此,我们描述了一种新的方法,该方法使用1,3-二溴-5,5-二甲基海因(DBH)作为溴源和氧化剂,从烯烃制备α-溴代酮。这种易于实施的两步一锅法在水中进行,能高产率地制备多种α-溴代酮。向中间体α-溴代酮中加入胺,还能通过一锅法制备α-氨基酮。

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