A ruthenium-catalyzed [1,2]-Brook rearrangement involved domino
sequence is presented to prepare highly functionalized silyloxy indenes
with atomic- and step-economy. This domino reaction is triggered by
acylsilane-directed C–H activation, and the aldehyde controlled
the subsequent enol cyclization/Brook Rearrangement other than β–H
elimination. The protocol tolerates a broad substitution pattern,
and the further synthetic elaboration of silyloxy indenes allows access
to a diverse range of interesting indene and indanone derivatives.