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Rh(Ⅲ)-catalyzed Chemo-divergent Coupling Of N-phenoxyacetamides And Alkylidenecyclopropanes Via C-H Activation

Posted on:2022-01-29Degree:MasterType:Thesis
Country:ChinaCandidate:Q ChenFull Text:PDF
GTID:2491306488998199Subject:Chemical Engineering
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Dihydrobenzofurans are important heterocyclic frameworks,which widely exist in natural products and bioactive molecules.It is one of the most interesting research areas for the construction of these structures.In the last two decades,transition-metal catalyzed C-H bond functionalization of arenes has been developed as a direct and effective strategy for the construction of C-C bond or C-X(X = N,O,S,etc.)bond,which could be used for the construction of complex functional molecules from commerically available materials.In this text,we developed Rh(III)-catalyzed C-H activation of N-phenoxyacetamides and chemo-divergent coupling with alkylidenecyclopropanes(ACPs).By taking advantage of the ring strain of ACPs,the coupling can be transannulative or non-annulative,delivering 3-ethylidenedihydrobenzofurans or dienes,respectively,under different reaction conditions,and the selectivity is mainly solvent-controlled.All the reactions can occurre under mild conditions with a broad substrate scope and excellent chemo-and diastereoselectivity.In the end,we studied the derivatization of the products and explored the reaction mechanism.
Keywords/Search Tags:Rhodium(Ⅲ) catalysis, N-phenoxyacetamide, alkylidenecyclopropanes cyclopropane, dihydrobenzofuran compounds, 1,3-diene products
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