Unveiling the Reactivity of Propargylic Hydroperoxides under Gold Catalysis

被引：48

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro ^{[2
]}

Teresa Quiros, M. ^{[1
]}

Lopez, Ramon ^{[3
]}

Menendez, Maria I. ^{[3
]}

Sochacka-Cwikla, Aleksandra ^{[1
,2
]}

机构：

[1] Univ Complutense Madrid, Dept Quim Organ 1, Unidad Asociada, Grp Lactamas & Heterociclos Bioact,CSIC,Fac Quim, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

[3] Univ Oviedo, Dept Quim Fis & Analit, Oviedo 33006, Asturias, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 02期

关键词：

ELECTRON-RICH ARENES; FRAGMENTATION; ACTIVATION; EFFICIENT; CHEMISTRY; MECHANISM; KETONES; ALKYNES;

D O I：

10.1021/ja3108966

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of beta-functionalized ketones. Moreover, the utility of some of the resulting products for the selective preparation of fused polycycles has been demonstrated. In addition, density functional theory (DFT) calculations and O-18-labeling experiments were performed to obtain an insight into various aspects of the controlled reactivity of propargylic hydroperoxides with external nudeophiles under gold catalysis.

引用

页码：898 / 905

页数：8

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