Palladium-Catalyzed Enantioselective Directed C(sp<sup>3</sup>)–H Functionalization Using C<sub>5</sub>-Substituted 8-Aminoquinoline Auxiliaries
Yi Huang, Xiaoyan Lv, Huarong Tong, Wen‐Ji He, Ziqian Bai, Hao Wang, Gang He, Gong Chen
Abstract
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 3 )–H functionalization reactions has been challenging. Herein, a new protocol is presented for the Pd-catalyzed enantioselective arylation of unactivated β C(sp 3 )–H bonds of alkyl carboxamides with aryl iodides using a C 5 -iodinated 8-aminoquinolines (IQ) auxiliary in conjugation with a BINOL ligand. Additionally, a C 5 -aryl substituted 8-aminoquinoline auxiliary can facilitate enantioselective alkenylation and alkynylation of benzylic C(sp 3 )–H bonds of 3-arylpropanamides with the corresponding bromide reagents under similar conditions.