Aerobic Palladium(II)-Catalyzed Dehydrogenation of Cyclohexene-1-carbonyl Indole Amides: An Indole-Directed Aromatization

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 gr...

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Veröffentlicht in:	Journal of organic chemistry 2012-10, Vol.77 (19), p.8750-8755
Hauptverfasser:	Kandukuri, Sandeep R, Oestreich, Martin
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Organic chemistry Preparations and properties Reactivity and mechanisms
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Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo301088f