Rh(I)-catalyzed Addition of the ortho C-H Bond in Aryl Sulfonamides to Maleimides

Abstract

The selective, Rh(I)-catalyzed ortho-C-H alkylation of biologically important aryl sulfonamides with maleimides with the aid of an 8-aminoquinoline directing group is reported. The reaction exhibits a good substrate scope.

Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation

“…Directed by 8‐aminoquinoline, Chatani developed the Rh(I)‐catalyzed ortho ‐alkylation of biologically important aryl sulfonamides with maleimides exhibiting broad substrate scope (Scheme 22). [28] Moreover, a series of deuterium labelling experiments were carried out to gain insights into the reaction mechanism.…”

Rh(i)- and Rh(ii)-catalyzed C–H alkylation of benzylamines with alkenes and its application in flow chemistry

“…Apart from the use of palladium, only a few examples of the use of other metals as catalysts, such as Co 2 h – j or Rh 2 f for annulation or alkynylation reactions with alkynes have been reported. Given our continuous interest in C–H alkylation reactions, 3 we were strongly motivated to investigate the ortho -alkylation of benzylamines with alkenes as alkyl sources, which, as of this writing, does not appear to have been reported ( Scheme 1b ).…”