Pd(II) or Pt(II)-Catalyzed Hydroarylation of Alkynes by Arenes.

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Efficient inter- and intramolecular hydroarylations of C-C triple bonds by simple electron-rich arenes have been realized in the presence of Pd (II) or Pt (II) catalysts and an acid such as trifluoroacetic acid and acetic acid. The reaction of heteroarenes such as pyrroles and indoles occurs under very mild conditions (e.g. at room temperature in neutral solvents such as CH2Cl2). The reaction provides a very good strategy for functionalization of arenes as well as heteroarenes, affording arylalkenes. The intramolecular reaction offers a concise and straightforward route to biologically interesting heterocycles such as coumarins, quinolinones and thiocoumarins. The possible mechanism involving electrophilic metalation of aromatic C-H bonds by a cationic metallic species such as [Pd (O2CCF3)] + and the formation of a vinyl cationic species is discussed.

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