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可见光促进的1,3-二羰基硫鎓叶立德的合成

Visible-Light-Promoted Synthesis of 1,3-Dicarbonyl Sulfoxonium Ylides.

作者信息

Echemendía Radell, de Oliveira Kleber T, Burtoloso Antonio C B

机构信息

Institute of Chemistry of São Carlos, University of São Paulo, CEP, 13560-970 São Carlos, SP, Brazil.

Department of Chemistry, Federal University of São Carlos, Campus São Carlos, 13565-905 São Carlos, SP, Brazil.

出版信息

Org Lett. 2022 Sep 9;24(35):6386-6390. doi: 10.1021/acs.orglett.2c02346. Epub 2022 Aug 26.

Abstract

A novel visible-light-promoted coupling of diazoketones with sulfoxonium ylides, employing a violet light-emitting diode, is described under both batch and continuous flow conditions. This transformation permits the direct synthesis of synthetically useful 1,3-dicarbonyl sulfoxonium ylides (33 examples, 21-85% yields), by means of an acylation from the and selective generation of ketenes. The reaction performed under flow conditions proved to be very efficient, providing the 1,3-dicarbonyl sulfoxonium ylides with higher yields and shorter reaction times.

摘要

本文描述了一种在间歇和连续流动条件下,使用紫色发光二极管可见光促进重氮酮与亚砜叶立德偶联的新方法。这种转化允许通过酰化反应和烯酮的选择性生成,直接合成具有合成用途的1,3 - 二羰基亚砜叶立德(33个例子,产率21 - 85%)。在流动条件下进行的反应被证明非常有效,能够以更高的产率和更短的反应时间得到1,3 - 二羰基亚砜叶立德。

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