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Synfacts 2017; 13(01): 0099
DOI: 10.1055/s-0036-1589770
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Spirocyclization of Alkyne-Tethered Aromatics with Silver Nitrate/Silica

Contributor(s):
Yasuhiro Uozumi
,
Go Hamasaka
Clarke AK, James MJ, O’Brien P, Taylor RJ. K, * Unsworth WP. * University of York, UK
Silica-Supported Silver Nitrate as a Highly Active Dearomatizing Spirocyclization Catalyst: Synergistic Alkyne Activation by Silver Nanoparticles and Silica.

Angew. Chem. Int. Ed. 2016;
55: 13798-13802
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Further Information

Publication History

Publication Date:
19 December 2016 (online)

 
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Key words

silver nitrate - silica gel - dearomatization - spirocyclization - heterogeneous catalysis - spiro compounds

Significance

Silica-supported silver nitrate ­(AgNO3/SiO2) catalyzed the dearomatizing spirocyclization of alkyne-tethered aromatics to give the corresponding spirocycles in 86–100% yield (eqs. 1–4).


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Comment

The continuous-flow reaction of 1-(1H-indol-3-yl)-4-phenylbut-3-yn-2-one on a column of AgNO3/SiO2 gave 5-phenyl-3H-spiro[cyclopent-4-ene-1,3′-indol]-3-one in quantitative yield (eq. 5).


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