Palladium-Catalyzed Enantioselective Directed C(sp3)–H Functionalization Using C5-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(sp3)–H functionalization reactions has been challenging. Herein, a new protocol is presented for the Pd-catalyzed enantioselective arylation of unactivated β C(sp3)–H bonds of alkyl carboxamides with aryl iodides using a C5-iodinated 8-aminoquinolines (IQ) auxiliary in conjugation with a BINOL ligand. Additionally, a C5-aryl substituted 8-aminoquinoline auxiliary can facilitate enantioselective alkenylation and alkynylation of benzylic C(sp3)–H bonds of 3-arylpropanamides with the corresponding bromide reagents under similar conditions.