超声辅助的布勒舍尔反应在水性和非水性介质中的应用：超声首次用于亲电芳香环化反应合成多并苯。

Ultrasound assisted Bradsher reaction in aqueous and non-aqueous media: First use of ultrasounds in electrophilic aromatic cyclisation leading to polyacenes.

作者信息

Kowalska Emilia, Bałczewski Piotr

机构信息

Group of Synthesis of Functional Materials, Department of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland; Department of Structural and Material Research, Institute of Chemistry, Environmental Protection and Biotechnology, The Faculty of Mathematics and Natural Sciences, Jan Długosz University in Częstochowa, Armii Krajowej 13/15, 42-201 Częstochowa, Poland.

出版信息

Ultrason Sonochem. 2017 Jan;34:743-753. doi: 10.1016/j.ultsonch.2016.07.010. Epub 2016 Jul 16.

DOI:10.1016/j.ultsonch.2016.07.010

PMID:27773301

Abstract

The present work describes the first use of ultrasounds in the Bradsher cyclisation of activated and non-activated ortho-formyl diarylmethanes. This reaction is also the first example of electrophilic, aromatic cyclisation assisted by ultrasounds which leads to pure polycyclic, fused aromatic hydrocarbons containing 3 and 4 fused rings in excellent yields. The reaction proceeds not only in aqueous but also in non-aqueous media at milder conditions (room temperature) and in much shorter reaction times than in conventional protocols.

摘要

本工作描述了超声首次用于活化和未活化的邻甲酰基二芳基甲烷的布拉德舍尔环化反应。该反应也是超声辅助亲电芳香环化反应的首个实例，此反应能以优异的产率生成纯净的含3个和4个稠环的多环稠合芳烃。该反应不仅能在水相中进行，也能在非水介质中于温和条件（室温）下进行，且反应时间比传统方法短得多。