| Indole compounds and their derivatives are heterocyclic alkaloids,they widely existing in natural products,drug molecules,dyes and functional materials.Because of their excellent chemical activity and wide application value,in recent years,indole has been one of the hotspots compound of chemical researchers.To development an effective strategies of indole C2 arylation has attracted more attention.Activation of carbon-carbon bond played an important role in the construction of synthetic natural product skeletons and realizing industrial production.Especially in the field of total synthesis of natural products,carbon-carbon bond activation is one of the most widely used methods.Compared with traditional carbon-hydrogen bond activation,activation of carbon-carbon bond needs high energy to overcome the bond energy and directional properties,so it has been a huge challenge to achieve carbon-carbon bond cleavage.With the excellent performance of transition metal catalysis of the chemical reactions was discovered by chemists,in recent years,the carbon-carbon bond activation strategies of transition metal catalysis such as palladium,rhodium,iridium and nickel have made great progress.With the research of the activation strategy of carbon-carbon bond catalyzed by transition metals,it has been found that the derect group as a functional group which can provide heteroatoms and coordinate with the metal center to stable metal complex intermediates and promote the breaking of carbon-carbon bond has attracted more attention.In this paper,we have developed an efficient rhodium(?)catalyzed system for indole C2 arylation of unstrained ketones via chelation-assisted C-C Bond cleavage.We introducing pyrimidine as the derected group,using cheap and readily available aryl borane and aryl silane as coupling reagent,we achieved to breaking carbon-carbon bond of indole C2 through Suzuki-Miyaura coupling and Hiyama coupling and realized arylation. |
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