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

TY - JOUR

T1 - Silica-Supported Silver Nitrate as a Highly Active Dearomatizing Spirocyclization Catalyst

T2 - Synergistic Alkyne Activation by Silver Nanoparticles and Silica

AU - Clarke, Aimee K

AU - James, Michael J

AU - O'Brien, Peter

AU - Taylor, Richard J K

AU - Unsworth, William P

N1 - © 2016, Wiley-VCH Verlag GmbH & Co. KG. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

PY - 2016/10/24

Y1 - 2016/10/24

N2 - 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.

AB - 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.

U2 - 10.1002/anie.201608263

DO - 10.1002/anie.201608263

M3 - Article

C2 - 27689850

SN - 1433-7851

VL - 55

SP - 13798

EP - 13802

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 44

ER -