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Domino C-H Functionalization Reactions of gem-Dibromoolefins: Synthesis of N-Fused Benzo[c]carbazoles

The development of a novel palladium-catalyzed domino reaction with indole-based gem-dibromoolefin substrates is described. The reaction allowed access to a new class of polycyclic nitrogen heterocycles: N-fused benzo[c]carbazoles. A key feature of this domino reaction was the participation of both bromides in C–H functionalization processes, a hitherto unprecedented reactivity. Various substituents and substitution patterns were tolerated in this reaction, allowing for a highly modular approach to these challenging synthetic targets. Mechanistic studies were performed to gain further insight into the reactivity of these systems and elucidate the sequence of reaction steps. The results indicate that isomerization of reaction intermediates likely played a key role in promoting a successful reaction.

Identiferoai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:OTU.1807/33248
Date20 November 2012
CreatorsHuang, Richard Yichong
ContributorsLautens, Mark
Source SetsLibrary and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada
Languageen_ca
Detected LanguageEnglish
TypeThesis

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