Photocatalytic oxygenation of olefins with oxygen isolation of 1,2-dioxetane and the photocatalytic O-O bond cleavage

被引：29

作者：

Ohkubo, Kei ^{[1
]}

Nanjo, Takashi ^{[1
]}

Fukuzumi, Shunichi ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, Japan Sci & Technol Agcy,SORST, Suita, Osaka 5650871, Japan

来源：

CATALYSIS TODAY | 2006年 / 117卷 / 1-3期

关键词：

dioxetane; electron transfer; oxygenation; radical coupling; olefin;

D O I：

10.1016/j.cattod.2006.05.056

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Formation of 1,2-dioxetane of tetraphenylethylene (TPE) occurs via formation of the electron transfer state of 9-mesityl-10-methylacridinium ion (Acr(+)-Mes) under visible light irradiation, followed by electron transfer from TPE to the Mes(center dot+) moiety together with electron transfer from the Acr(center dot) moiety to O-2, and the subsequent radical coupling between TPE center dot+ and O-2(center dot-) to yield the corresponding 1,2-dioxetane. The dioxetane thus formed was isolated using column chromatography. Photooxygenation of stilbene derivatives is also efficiently catalyzed by Acr(+)-Mes, accompanied by efficient cis-trans isomerization, to afford the corresponding benzaldehydes via electron transfer from Acr(center dot)-Mes(center dot+) to stilbene derivatives. and oxygen. (C) 2006 Elsevier B.V. All rights reserved.

引用

页码：356 / 361

页数：6

共 78 条

[1] A highly diastereoselective dioxetane formation by the hydroxy-directed [2+2] cycloaddition of singlet oxygen to a chiral allylic alcohol [J].