The use of enaminones as effective synthons for a directed C-H functionalization is reported. Proof-of-concept protocols have been developed for the Rh(III) -catalyzed synthesis of naphthalenes, based on the coupling of enaminones with either alkynes or α-diazo-β-ketoesters. Two inherently reactive functionalities (hydroxy and aldehyde groups) are integrated into the newly formed cyclic framework and a broad range of substituents are tolerated, rendering target products readily available for further elaboration.
Cobaltacycle synthesis via C-H activation has been achieved for the first time, providing key mechanistic insight into cobalt catalytic chemistry. N-Chloroamides are used as a directing synthon for cobalt-catalyzed room-temperature C-H activation and construction of heterocycles. Alkynes as coupling partners allow convenient access to isoquinolones, a class of synthetically and pharmaceutically important compounds. The broad substrate scope enables a diverse range of substitution patterns to be incorporated into the heterocyclic scaffold.
A distinct C-H activation-based traceless synthetic protocol via electrophilic removal of a directing group is reported, complementing the currently exclusively used nucleophilic strategy. Rh(III)-catalyzed, N-nitroso-directed C-H activation allows the development of a traceless, atom- and step-economic, cascade approach for the synthesis of indole skeletons, starting from readily available N-nitroso and α-diazo-β-keto compounds. Importantly, the cyclization/denitrosation reaction represents a hitherto unobserved reactivity pattern for the N-nitroso group.
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