Palladium-Catalyzed Enantioselective Directed C(sp)-H Functionalization Using C-Substituted 8-Aminoquinoline Auxiliaries.

8-Aminoquinoline (AQ) has proven to be a highly effective bidentate directing group for palladium-catalyzed C-H functionalization reactions. However, enantiocontrol of AQ-directed C(sp)-H functionalization reactions has been challenging. Herein, a new protocol is presented for the Pd-catalyzed enantioselective arylation of unactivated β C(sp)-H bonds of alkyl carboxamides with aryl iodides using a C-iodinated 8-aminoquinolines (IQ) auxiliary in conjugation with a BINOL ligand. Additionally, a C-aryl substituted 8-aminoquinoline auxiliary can facilitate enantioselective alkenylation and alkynylation of benzylic C(sp)-H bonds of 3-arylpropanamides with the corresponding bromide reagents under similar conditions.