Enantioselective C,P-Palladacycle-Catalyzed Arylation of Imines

Yinhua Huang; Lijun Wang; Junbao Li; Huayu Qiu; Pak-Hing Leung

doi:10.1021/acsomega.0c01124

Enantioselective C,P-Palladacycle-Catalyzed Arylation of Imines

ACS Omega. 2020 Jun 23;5(26):15936-15941. doi: 10.1021/acsomega.0c01124. eCollection 2020 Jul 7.

Authors

Yinhua Huang¹, Lijun Wang¹, Junbao Li¹, Huayu Qiu¹, Pak-Hing Leung²

Affiliations

¹ College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, China.
² Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.

Abstract

Chiral diarylmethylamines are of great interest because of their prevalence in biological and pharmaceutical sciences. Herein, we report a C,P-palladacycle-catalyzed enantioselective synthesis of chiral diarylmethylamines via asymmetric arylation of N-protected imines with arylboronic acids. The C,P-palladacycle showed high reactivity (up to 99% yield) and enantioselectivity (up to 99% ee) toward this arylation, enabling the tolerance of a wide range of functionalities, providing a convenient and efficient access to enantiomerically enriched diarylmethylamines. The absolute configuration of the product was well rationalized by the proposed stereochemical pathway and the catalytical cycle.