Domino carbopalladation-cross-coupling for the synthesis of 3,3-disubstituted oxindoles.
This study examines a domino carbopalladation-cross-coupling reaction for the formation of valuable oxindole scaffolds. Furthermore, the reaction sequence forges vicinal stereocenters in a stereospecific manner through the formation of two carbon-carbon bonds and, thereby, rapidly generates complexity. The reaction gives high yields for a variety of acrylamide substrates, and various organoboranes have also been evaluated for the cross-coupling. This work offers insight into the relative rates determining a successful carbopalladation-cross-coupling reaction and how to favor the desired reaction pathway.
Chemical Science and Engineering, Organic Chemistry, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden.
Brinton
B
Seashore-Ludlow
Peter
P
Somfai