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Spirocyclization of Alkyne-Tethered Aromatics with Silver Nitrate/Silica
Silica-Supported Silver Nitrate as a Highly Active Dearomatizing Spirocyclization Catalyst: Synergistic Alkyne Activation by Silver Nanoparticles and Silica.
Angew. Chem. Int. Ed. 2016;
19 December 2016 (online)
Key wordssilver nitrate - silica gel - dearomatization - spirocyclization - heterogeneous catalysis - spiro compounds
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).
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).