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苄基磷酸酯在与活性和非活性芳烃的傅克反应中的应用:多芳基化烷烃的合成方法

Benzylic Phosphates in Friedel-Crafts Reactions with Activated and Unactivated Arenes: Access to Polyarylated Alkanes.

作者信息

Pallikonda Gangaram, Chakravartya Manab

机构信息

Department of Chemistry, Birla Institute of Technology and Sciences , Pilani Hyderabad Campus, Jawahar nagar, Shameerpet Mandal, Hyderabad, Telangana 500078, India.

出版信息

J Org Chem. 2016 Mar 4;81(5):2135-42. doi: 10.1021/acs.joc.5b02441. Epub 2016 Feb 16.

DOI:10.1021/acs.joc.5b02441
PMID:26835977
Abstract

Easily reachable electron-poor/rich primary and secondary benzylic phosphates are suitably used as substrates for Friedel-Crafts benzylation reactions with only 1.2 equiv activated/deactivated arenes (no additional solvent) to access structurally and electronically diverse polyarylated alkanes with excellent yields and selectivities at room temperature. Specifically, diversely substituted di/triarylmethanes are generated within 2-30 min using this approach. A wide number of electron-poor polyarylated alkanes are easily accomplished through this route by just tuning the phosphates.

摘要

易于获得的贫电子/富电子伯和仲苄基磷酸酯适合用作傅克苄基化反应的底物,仅需1.2当量的活化/钝化芳烃(无需额外溶剂),就能在室温下以优异的产率和选择性得到结构和电子性质多样的多芳基化烷烃。具体而言,使用这种方法可在2至30分钟内生成各种取代的二芳基甲烷/三芳基甲烷。通过调整磷酸酯,通过这条路线可以轻松实现大量贫电子多芳基化烷烃的合成。

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