Pd-Catalyzed Sequential
C–C Bond Formation
and Cleavage: Evidence for an Unexpected Generation of Arylpalladium(II)
Species
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Abstract
A Pd(II)-catalyzed reaction engaging alkenyl β-keto
esters
is reported that leads to the formation of 1-naphthols and an unexpected
generation of arylpalladium(II) species. Interception of the in situ
generated arylpalladium(II) species in a Mizoroki–Heck reaction,
together with additional mechanistic studies, provided strong evidence
in support of the first <i>aromatization-driven</i> β-carbon
elimination process. A single Pd catalyst served to promote a series
of both C–C bond forming and cleavage events in an unprecedented
manner