Silica-Supported Silver Nitrate as a Highly Active Dearomatizing Spirocyclization Catalyst: Synergistic Alkyne Activation by Silver Nanoparticles and Silica

被引：95

作者：

Clarke, Aimee K. ^{[1
]}

James, Michael J. ^{[1
]}

Brien, Peter O. Q. ^{[1
]}

Taylor, Richard J. K. ^{[1
]}

Unsworth, William P. ^{[1
]}

机构：

[1] Univ York, York YO10 5DD, N Yorkshire, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 44期

关键词：

dearomatization; flow chemistry; heterogeneous catalysis; silver nanoparticles; spirocycles; ASYMMETRIC ALLYLIC DEAROMATIZATION; ENANTIOSELECTIVE SYNTHESIS; SELECTIVE SYNTHESIS; EFFICIENT; INDOLENINES; CARBAZOLES; ALCOHOLS; STRATEGY; PYRROLES; ACCESS;

D O I：

10.1002/anie.201608263

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Silica-supported AgNO3 (AgNO3-SiO2) catalyzes the dearomatizing spirocyclization of alkyne-tethered aromatics far more effectively than the analogous unsupported reagent; in many cases, reactions which fail using unsupported AgNO3 proceed effectively with AgNO3-SiO2. Mechanistic studies indicate that this is a consequence of silver nanoparticle formation on the silica surface combined with a synergistic effect caused by the silica support itself. The remarkable ease with which the reagent can be prepared and used is likely to be of much synthetic importance, in particular, by making nanoparticle catalysis more accessible to non-specialists.

引用

页码：13798 / 13802

页数：5

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