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Formation Of Multi-ring Systems Via DDQ-mediated Cross-Dehydrogenative Coupling Reaction

Posted on:2013-02-09Degree:MasterType:Thesis
Country:ChinaCandidate:L CaoFull Text:PDF
GTID:2211330371954163Subject:Pharmaceutical Engineering and Technology
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This dissertation mainly focuses on the study of building muti-ring systems via DDQ-mediated cross-dehydrogenative coupling reaction. It is consisted of the following three aspects:1. Constructing polysubstituted naphthalenes by DDQ-mediated cross-dehydrogenative coupling reactionWe demonstrated a novel iron-catalyzed tandem cross-dehydrogenative coupling and benzoannulation process for the synthesis of biologically and synthetically important polysubstituted naphthalene derivatives. This method could increase molecular complexity and construct multiple C-C bonds in one pot reaction. Added nucleophile, this reaction undertook successively the process of DDQ oxidation, nucleophilic attack, intramolecular Friedel-Crafts cyclization, double-bond migration and dehydrogenative aromatization to afford polysubstituted naphthalene derivatives.2. Constructing polysubstituted cyclopentenes through DDQ-mediated cross-dehydro-genative coupling reactionWe developed an iron-catalyzed cross-dehydrogenative coupling reaction building multi-substituted cyclopentenes. The sp3 C-H bond of 1,2-diarylpropylene was activated by DDQ to form carbocation intermediate, which was attacked subsequently by 1,2-diarylpropylene to form multi-substituted cyclopentene derivatives before intramolecular cyclization.3. Constructing polysubstituted indenes via DDQ-mediated cross-dehydrogenative coupling reactionWe developed a simple and effective method, which employed copper catalyst to the intramolecular cross-dehydrogenation coupling reaction of 1,2,3-triarylpropylene to prepare polysubstituted indenes. This protocol enriched the application of copper catalysts in the C-H activation and extended the use of DDQ in organic synthesis.
Keywords/Search Tags:Cross-Dehydrogenative Coupling, 2,3-dichloro-5,6-dicyanobenzoquinone, C-H activation, Naphthalene derivatives, Cyclopentene derivatives, Indene derivatives
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