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有机硒与4-二甲氨基吡啶共催化:从未活化烯烃区域选择性合成中等大小的卤代内酯和溴代氧杂环庚烷。

Organoselenium and DMAP co-catalysis: regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes.

作者信息

Verma Ajay, Jana Sadhan, Prasad Ch Durga, Yadav Abhimanyu, Kumar Sangit

机构信息

Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal, Madhya Pradesh 462066, India.

出版信息

Chem Commun (Camb). 2016 Mar 18;52(22):4179-82. doi: 10.1039/c5cc10245f.

Abstract

A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. (77)Se NMR, mass spectrometry and theoretical studies reveal that the reaction proceeds via a quaternary selenium intermediate.

摘要

一种由双(4-甲氧基苯基)硒化物和4-(二甲基氨基)吡啶(DMAP)组成的催化体系已被开发用于区域选择性合成具有高跨环张力的中等大小的溴代/碘代内酯和溴代氧杂环庚烷。(77)Se核磁共振、质谱和理论研究表明,该反应通过季硒中间体进行。

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