Ligand-Controlled Regioselective Pd-Catalyzed Diamination of Alkenes

Xiaojian Liu; Chuanqi Hou; Yiyuan Peng; Pinhong Chen; Guosheng Liu

doi:10.1021/acs.orglett.0c03634

Ligand-Controlled Regioselective Pd-Catalyzed Diamination of Alkenes

Org Lett. 2020 Dec 4;22(23):9371-9375. doi: 10.1021/acs.orglett.0c03634. Epub 2020 Nov 12.

Authors

Xiaojian Liu¹, Chuanqi Hou², Yiyuan Peng¹, Pinhong Chen², Guosheng Liu²

Affiliations

¹ Key Laboratory of Functional Small Organic Molecules, Ministry of Education, Jiangxi Province's Key Laboratory of Green Chemistry, Jiangxi Normal University, Nanchang 330022, China.
² State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

PMID: 33179502
DOI: 10.1021/acs.orglett.0c03634

Abstract

A ligand-controlled system has been disclosed for the regioselective palladium-catalyzed diamination of unactivated alkenes, which provides an easy access to a variety of amino-functionalized piperidines and pyrrolidines. The steric hindrance of ligands controlled the regioselectivtities of products. 6-Endo diamination occurred with less sterically hindered quinox ligand to afford 3-aminopiperidines, while 5-exo diamination occurred with sterically bulky pyox ligand to give amino-substituted pyrrolidines.