AgF‐Mediated Dialkylation of Activate Alkenes: An Efficient Access to Nitrile‐Containing Spirooxindoles

Abstract

A novel Ag-mediated dialkylation reaction of alkenes was disclosed, in which AgF was essential to activate C-H bond of acetonitrile. This reaction provided an efficient way to nitrile-containing spirooxindoles from readily available (1H-indol-3-yl)methanamine derivatives.

A novel coupling reaction of α-halo ketones promoted by SmI3/CuI

“…A further O 18 labeling experiment (entry 7) showed that the O 18 can not be detected in the product 2a when the reaction was carried out in the presence of H 2 O 18 which was oen used to identify the source of oxygen in the product. 12 Besides, the investigation also showed that no byproduct can be observed yet when the reaction was carried out in the presence of some additional additives such as NH 3 $H 2 O (entry 8) or CH 3 OH (entry 9) respectively. These results should be crucial to demonstrate the role of DMF in the mechanism.…”

Transition metal-catalyzed synthesis of spirooxindoles

“…A novel method for the synthesis of nitrile-containing spirooxindoles 5 mediated by AgF was developed by Liu and co-worker. 35 Activated alkenes 4 were dialkylated with acetonitrile as solvent, 4 equiv. of AgF as catalyst in an atmosphere of nitrogen at 110 °C in which the C–H bond of acetonitrile was activated by AgF ( Scheme 2 ).…”