Bridging C-H Activation: Mild and Versatile Cleavage of the 8-Aminoquinoline Directing Group

Abstract

8-Aminoquinoline has emerged as one of the most powerful bidentate directing groups in history of C-H activation within the last decade. However, cleavage of its robust amide bond has shown to be challenging in several cases, thus jeopardizing the general synthetic utility of the method. To overcome this limitation, we herein report a simple oxidative deprotection protocol. This transformation rapidly converts the robust amide to a labile imide, allowing subsequent cleavage in a simple one-pot fashion to rapidly access carboxylic acids or amides as final products.

Keywords: 8-aminoquinoline; C−H activation; cleavage; directing group; ozonolysis.