Aerobic Palladium(II)-Catalyzed
Dehydrogenation of
Cyclohexene-1-carbonyl Indole Amides: An Indole-Directed Aromatization
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Abstract
A palladium(II)-catalyzed oxidative dehydrogenation of
cyclohexene-1-carbonyl
indole amides yielding the corresponding benzoylindoles is reported.
The new aromatization is also applied to functionalized indoles such
as tryptamine and tryptophan. The tethered indole is likely acting
as a directing group for allylic C–H bond activation, and there
is evidence for a mechanism proceeding through 1,3-diene formation
followed by aromatization