A novel and inexpensive method of nontoxic, silver-salt-catalyzed carboazidation of arylacrylamides to afford corresponding azide oxindoles is reported. This reaction system exhibits great functional group tolerance. All products form a crucial skeleton for the synthesis of various indole alkaloids.

ABSTRACT[RhCp*Cl 2 ] 2 can catalyze the oxidative coupling of N-aryl and N-alkyl benzamidines with alkynes to give N-substituted 1-aminoisoquinolines in high selectivity.Transition-metal catalyzed organic reactions via activation of CÀH bonds have attracted increasing attention. 1 This process is attractive in that CÀH bonds are ubiquitous and prefunctionalization of CÀH bonds is no longer necessary. Therefore, selective and efficient functionalization of CÀH bonds under mild conditions has been long sought, and this should allow the construction of complex molecules in an energy-efficient and step-economic fashion. Significant progresses have been made, and this topic has been extensively reviewed. 2 Among the various promising activation strategies is the utilization of a proximal directing group, which facilitates the activation of substrate ortho CÀH bonds. By utilizing this strategy with oxygen and nitrogen directing groups, rhodium complexes have stood out as efficient catalysts in the functionalization of CÀH bonds using unsaturated coupling partners. 3 Recently, Rh(III)-catalyzed oxidative CÀH functionalization of arenes with alkynes has been increasingly explored, which allowed for the synthesis of a broad spectrum of heterocycles. 4 A number of research groups, including ours, 5 have successfully applied this method to the synthesis of isoquinolines, 6 isoquinolones, 5c,7 indoles, 8 isocoumarins, 9 indenols, 4b,d pyrroles, 10 and pyridones. 5d,11 † The Chinese Academy of Sciences. ‡ Northwest Normal University.