用于固体负载底物上多键二酰亚胺还原的改进方法。
Improved method for the diimide reduction of multiple bonds on solid-supported substrates.
作者信息
Buszek Keith R, Brown Neil
机构信息
Department of Chemistry, Kansas State University, 111 Willard Hall, Manhattan, Kansas 66506, USA.
出版信息
J Org Chem. 2007 Apr 13;72(8):3125-8. doi: 10.1021/jo0622173. Epub 2007 Mar 17.
Abstract
A mild and improved method for reducing multiple bonds on various resins with diimide is described. The simple procedure readily generates diimide from 2-nitrobenzenesulfonohydrazide and triethylamine at room temperature. A number of representative multiple bonds in various steric and electronic environments were examined, including polar double bonds such as carbonyl and azo, for ease and selectivity of reduction. A general trend of reactivity was identified which revealed, inter alia, that terminal olefins, 1,2-disubstituted olefins, electron-poor olefins, and terminal alkynes were the most easily reduced.
摘要
描述了一种温和且改进的用二酰亚胺还原各种树脂上多重键的方法。该简单程序在室温下能由2-硝基苯磺酰肼和三乙胺轻松生成二酰亚胺。研究了各种空间和电子环境中的许多代表性多重键，包括羰基和偶氮等极性双键，以考察还原的难易程度和选择性。确定了一种一般的反应活性趋势，尤其表明末端烯烃、1,2-二取代烯烃、缺电子烯烃和末端炔烃最容易被还原。
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3
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Org Lett. 2002 May 16;4(10):1771-4. doi: 10.1021/ol025844x.
4
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