Rh(III)-Catalyzed [3+2] Annulation of Aniline Derivatives with Vinylsilanes via C-H Activation/Alkene Cyclization: Access to Highly Regioselective Indoline Derivatives

The Rh(III)-catalyzed reaction of aniline derivatives that contain a pyrimidine directing group with vinylsilanes results in the formation of C3-substituted indoline derivatives in a highly regioselective manner via a C-H activation/alkene cyclization cascade. The results of the mechanistic experiments indicate that C-H bond cleavage is not the rate-determining step and that the reaction proceeds via the formation of a six-membered rhodacycle as a key catalytic species through a pyrimidine-directed electrophilic ortho-C-H rhodation.

Automated summary

The Rh(III)-catalyzed reaction of aniline derivatives containing a pyrimidine directing group with vinylsilanes leads to the formation of C3-substituted indoline derivatives via a highly regioselective C-H activation/alkene cyclization cascade. Mechanistic experiments suggest that C-H bond cleavage is not the rate-determining step, but rather the reaction proceeds through the formation of a six-membered rhodacycle as a key catalytic species via pyrimidine-directed electrophilic ortho-C-H rhodation.