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通过铜(I)催化的芳基烯烃与叔丁基过氧化氢的氧化/叔丁氧基化反应高度选择性合成2-叔丁氧基-1-芳基乙酮

Highly Selective Synthesis of 2--Butoxy-1-Arylethanones via Copper(I)-Catalyzed Oxidation/-Butoxylation of Aryl Olefins with TBHP.

作者信息

Zhang Jiantao, Xiao Duoduo, Tan Hua, Liu Weibing

机构信息

College of Chemistry, Guangdong University of Petrochemical Technology, Guandu Road, Maoming 525000, People's Republic of China.

出版信息

J Org Chem. 2020 Mar 6;85(5):3929-3935. doi: 10.1021/acs.joc.9b03156. Epub 2020 Feb 19.

Abstract

A practical and environmentally friendly protocol for the selective oxidation of aryl olefins to arylethanone derivatives by using a Cu(I) catalyst and -butyl hydroperoxide (TBHP) has been developed. A series of 2--butoxy-1-arylethanones were obtained in moderate to good yields under mild conditions with high selectivity. In this method, TBHP acts not only as an oxidant but also as the -butoxy and carbonyl oxygen sources. This enables one-step oxidation/-butoxylation. Various allyl peroxides were also synthesized from allyl substrates.

摘要

已开发出一种实用且环境友好的方法,使用铜(I)催化剂和叔丁基过氧化氢(TBHP)将芳基烯烃选择性氧化为芳基乙酮衍生物。在温和条件下以中等至良好的产率和高选择性获得了一系列2-叔丁氧基-1-芳基乙酮。在该方法中,TBHP不仅作为氧化剂,还作为叔丁氧基和羰基氧源。这实现了一步氧化/叔丁氧基化反应。还从烯丙基底物合成了各种烯丙基过氧化物。

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