Catalytic C-C Cleavage/Alkyne-Carbonyl Metathesis Sequence of Cyclobutanones

Org Lett. 2020 May 15;22(10):3993-3999. doi: 10.1021/acs.orglett.0c01317. Epub 2020 Apr 30.

Abstract

A ring-opening/alkyne-carbonyl metathesis sequence of alkyne-tethered cyclobutanones catalyzed by AgSbF6 is realized for the first time to furnish multisubstituted naphthyl ketones under mild conditions. A range of substrates decorated with various substituents at different positions were all well accommodated. Preliminary mechanistic studies show that silver salt acted as a Lewis acid to facilitate both C-C cleavage of the cyclobutanone moiety and the subsequent metathesis between C═O and C≡C bonds.

Publication types

  • Research Support, Non-U.S. Gov't